I usually recommend clients a pretty easy cosmetic rehab which is refinish floors, replace cabinets with modern white ones, add a white stone, new appliances, new bathroom vanity/mirror/light fixture and add in unit laundry. 

However, a town of that size is very similar to the areas that we have funded a lot of rehab and DSCR deals.What are some of the things that you like about what you're seeing in the Winchester market for a BRRRR?

Great advice, I found that the professional photos and doing the rehab slightly above the competition really seemed to help as I had almost 0 vacancy! 

For short term rentals, I use: AirDNA: I love AirDNA, but don't love the address search.

My biggest tip is to save way more that you make and then buy a 2-4 unit building and use a 203k or homestyle renovation loan to do some rehab and add some instant equity.Also, Network as much as possible and get comfortable approach any one and asking lots of questions. 

Let any potential renter know that you intend to convert the garage into an ADU and address any potential issues created by adding the ADU (parking, shared yard, quiet hours, etc.)

Any tips on avoiding unexpected costs or delays during rehab?

if done right, you'll likely break even each month on rent, and you'll have the equity you created via the rehab. 

I'd say $10,000 - $15,000 in rehab.

They remain available to assist investors throughout the investment lifecycle, whether it involves refinancing options, addressing financial concerns, or facilitating future funding needs.