This strategy is not well liked on BP and I am not a fan of it as I just do not see ability to make money in this.

If you treat it as a rental, you give up the homestead break but you gain depreciation, expense deductions, and the ability to show rental losses that might offset other income depending on your situation.Since your child is living there, many parents keep it under the homestead rules for the tax savings and simplicity, especially if the rent from friends just helps cover expenses.

In this setup, personal creditors attempting to go after the assets in the FL LLC will first have to get through the WY LLC which can be a pretty tall order.Third, as to due-on-sale issues, your options/ability to transfer the property into an LLC largely depends on whether the loan is backed by Freddie Mac or Fannie Mae.

My question is if it would hurt my loan ability from the next lender we use if we have the roof payments still going that had to have financed through the contractor? 

If you already have cash and construction ability, you’re in a great position to move fast when a deal pencils out.

If you have the ability to buy out of state which is actually easier and costs less I would check out some other states like IN, OH, TN, FL, NV, NC, GA and a few others. 

There are always exceptions but the most realistic scenario if you find one of those needles is the ability to do a walk-through and close quickly because there are hundreds of buyers looking for the same deal in Philadelphia all willing to move quick. 

There are certainly a lot of benefits that the OBBA brings to MA residents who are looking to acquire a STR.The first conversation you want to have with your accountant is what you need to do to treat the property as active instead of passive(if that is what you are looking to achieve).The other benefit of the OBBA is the increased ability to write off state and local taxes as part of the itemized deduction.Best of luck to you in your search!

We are selling our current home and downsizing, which should help jumpstart our ability to get started with a business through selling our primary residence. 

I’m a strong proponent of Short-Term Rentals (STRs) when structured correctly, as they can offer significant tax advantages — particularly the ability to generate non-passive income without qualifying as a Real Estate Professional.To fully benefit from this strategy, it's important that you:Actively participate in managing the property, andMaintain detailed records and logs to document your material participation hours (e.g., time spent on guest communications, cleaning coordination, repairs, marketing, etc.).Proper documentation not only supports your position in the event of an audit, but it’s also essential for meeting the IRS thresholds for material participation under the STR exception.happy to help.