My only question (if you know the answer) is now that the assessments have been rolled back, will property taxes be rolled back for this year... or will it start in 2026?

Maybe this is pretty simple answer but I always appreciate the depth of knowledge of BiggerPockets!

Check out my profile and I am in Florida as well so feel free to give me a call or send me an email.I can help answer your questions and give you a few tips to avoid lost time and money!

This doesn't answer the question, but if you just moved to Worcester, you should connect with @Andrew Freed because he has a lot of meetups going in your area and is an active investor.On the cleaning company, it would be a great ancillary after you've been in the area a while and met other STR owners.

This is the place to get answers

Ironically, you witnessed that asking your professionals did not produce a clear answer, and even asking specialized tax professionals on this forum resulted in a bit of a disagreement. 

I look forward to your answers and also any other general advice on keeping my cost low whilst maintaining quality with renovations would be much appreciated.Thanks!

Boy what a lot of great answers.

@Mel Rosario, like you said, it's difficult to give a correct answer or know how local markets will perform in the future to provide further advice than whether this strategy fits your criteria and aligns with your future retirement goals.

Snow the short answer, yes.The VA guidelines say you need to have prior landlord experience in order to use rental income towards qualifying.