Are you looking to get an investment property at 20% down or a primary residence you can house hack (rent the rooms in the house you are living in), or a primary residence (better for people who are married/have kids/don't want roommates) where you live in it for 12 months then rent it when you buy your next property to repeat the process.

We would greatly appreciate feedback from the many professionals and experts on here.https://www.airbnb.com/rooms/1178092575708761168?

I would mention here that a typical condo or single family does not qualify for the Act 60 TOURISM tax credit (which gives you up to 40% back)  - the project needs to meet certain qualifications as a guest house, hotel, villas or bed & breakfast - it can be as little as 3 rooms.  

The attached images show the attic's current condition.The room in the back is insulated and and would require finished flooring, heat, & paint (62 sqft above 7 ft height). 

Considerations:-Cost to build at $350/sqft -Estimated value of 1,000sqft DADU (3bd / 2ba) after completion: $600K-Estimated after completion value of 2,000sqft single family (4bd / 3ba): $900K-Estimated after completion value of 1,000sqft ADU (3bd / 2ba) after completion: $550K The real question is, how accurate are the numbers and how much wiggle room do you have.

(i.e. have RE prices increased in the area, is there room for additional appreciation, how is the STR and LT rental market, any new housing or commercial developments?

That's a more difficult sell.You're likely going to have to rent it out as individual rooms, perhaps to local college students. 

So far I've notice some towns have regulations or already blocking STR like Woodstock, thing is that those are saturated markets already and no room for STR (IMO), but catskills is so big its a matter of a location and price! 

I have a rental with ceiling fans in every room, I am afraid if they start making noise, or don't produce enough air for tenants liking I will get complaints and they will ask me to replace them. 

Hello BP members, I live in a SFH close to Sugar Land area in Houston TX, and I'm looking to rent two rooms out of a single family home I currently reside in.