I'd suggest watching the Nest installation video. It'll give you a decent baseline of what you're supposed to be paying attention to once you start looking deeper.
Your best entry level options for upgrading to a more modern thermostat are likely Honeywell, Nest and Ecobee. Nest and Ecobee are the more modern ones, but do not always play nice with older HVAC systems. Honeywell has some smart options, but if those are not available, Honeywell has some thermostats that work better with older HVAC systems, but I don't know if you'd be able to do that AND have smart features (ie: Access from an app).
If you get someone to install a thermostat, I think you'll end up paying at least $100-150 for that service. If that person needs to pull a bundle of wires to do it properly, then the numbers can go crazy if you're paying their billing rate x several hours of swear laden grief on their side for pulling lines or the thermostat inexplicably not working even though it's supposed to (ie: 3-6 hours time overruns). That's not even factoring in the materials and the cost of a thermostat which is likely around $200-300 total. I've asked a few HVAC guys for a quote in the past. Most are very busy right now and most refuse to even offering a quote. You might be able to hire someone who knows how to fish wires to pull a bundle for you at a lower charge out rate, but be aware the scenario for just sorting out a smart thermostat could range from $400 to $900 all in depending if you run into compatibility issues.
If you have the option, Nest is a little funky at times, but does have power steal options if you don't have a common wire. Just make sure the thermostat doesn't run out of power if it cannot steal enough power (can pull it off and charge via cable).
Ecobee is what I'd go with if I could get a mulligan and I'd pay the stupid money to pull new bundles and hook up a C wire. I currently have an 80s era HVAC and a new AC unit and I have a wireless hook up to an analog HVAC fan switch.
I have a Nest collecting dust as it was replaced by an older style Honeywell thermostat with no smart app. This was because the Nest and Ecobee weren't compatible with my 80s era set up per the HVAC AC installer. I'm likely primed for a full on HVAC/Utility room overhaul in the next 3-5 years though. I'll get everything replaced and redone to the nines and then get Ecobees to replace the Honeywell and my other Nest.
I would highly recommend that you don't get the "lite" versions of the Nest and Ecobee. They seem to only have as many if not less features than a basic Honeywell thermostat and their only benefit is the app on a phone that allows temp control from phone and scheduling. I believe it's less than half the features of a typical Nest/Ecobee.
IIRC, the lite versions are not as compatible with as many things as the full versions by a lot. I don't know about the latest ones, but the older ones couldn't do a lot of different HVAC systems, AC systems, multi room temp sensors, smart vents and humidifiers whether they are brand new or old. The app it uses isn't even the actual full thermostat app IIRC, it's some seriously hacked down version. This loses certain features like accurate auto away eco mode, motion sensing, accurate usage tracking etc.
I believe the sole benefit of the lite versions is that it uses AA batteries rather than common wire/internal battery, but beyond that, it's like paying 66% of the full version for 33% of the features.
Last time I tinkered around with the thermostat stuff, it was surprisingly a bigger PITA than expected. It took me a long time to figure it out, but I had an idea how to figure it out. If you need to chat with an expert though, EVERLAST on the site is probably a good person to PM to ask who to contact to ask a few minutes worth of questions or who he knows might be able to help you out.
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