We mutually aggreged to a new lease with a higher rent, as he wants to receive the voucher so looks like we are on a good road to some resolution here.  

It can also be beneficial to join local facebook groups for investing.

The policy is from Mass Mutual fwiw.

Benefits:-Beneficial tax implication since you won't be realizing your gain.

That said, we have seen the following work:An attorney prepares a land trust (intervivos revocable trust) for the subject property and after the deed into trust is recorded, the trustee (the seller) will quit their trustee position, and the beneficiaries (usually the seller) name a new trustee (the buyer) and transfer their beneficial interest to the buyer.By using the trust, one legally avoids the due-on-sale clause. 

If you have to cover more than market rent on your own it still might be beneficial to own but you are taking on risk if the rents in the area are not increasing or you want to move out.

His final determination (3rd choice) was Schedule E, although this is not what i expected and is not nearly as beneficial when it comes to writing off expenses towards my income / lowering AGI as schedule C.

If anyone has insights, experiences, or can recommend specific platforms or techniques beneficial for marketing unique luxury vacation rentals, your guidance would be highly appreciated.Thank you for sharing your expertise!

However, if you don't have much experience with purchasing real estate, or are unfamiliar with your local area, then it may be beneficial for you to work with an agent regardless of where you are sourcing your deals from.Your agent should be providing value beyond whatever amount they are charging you, and if they're not it may be time to find someone new to join your team!

Stephanie:Let's give two extreme examples:1) A person buys a mutual fund in their IRA.