@Ryan Cotterill to help answer some of your questions, let me see if I can help.
Yes, housing prices have gone up considerably. We just got numbers for November of 2021 and inventory is down 45.4% over a year ago, median price is up 20%, volue of sales is up over 30%...so it is very active and prices are continuing to rise. With the new Fannie Mae rules going into effect, this will curb some of the investors buying and allow homeowners more of a chance, but I don't see prices coming down.
For looking on Zillow, I think 25 miles out from Disney is way too far. First off, you can't airbnb in Orange County (for the most part), so you have to stick to Lake, Osceola and Polk and I would stick to 10 miles out if you want a high performing unit. More than that and the traffic is a nightmare! I see that the bigger homes are likely out of your budget, my advice is always buy as big as you can afford, you can always rent it out as a 'smaller' unit in non peak times, but there are simply less of the bigger units and you won't be competing on nightly rates with smaller units that want to rate cut their competitors.
For self managing, there is a big learning curve. Unless you have the time to learn everything and have contacts for all the trades and apps and software you will need, I think it is best to hire a PM until you get a grasp on how it all works and let them build your reviews and presence.
Hope this helps, Good luck!