Work with a qualified intermediary and tax advisor to ensure compliance and optimize your strategy.

.🔹 Property Tax Relief – If your property is severely damaged, you may qualify for reassessment and potential tax refunds.

One area can show great signs but literally cross the railroad tracks and it’s a different world.Be aware of these types of physical delineation.If you are getting no demand from qualified applicants then I would say it’s not in a margin of a gentrifying neighborhood.  

As already mentioned, he wouldn't be able to use rent from roommates to help qualify but based on the numbers you shared there should be a VA option available considering how much flexibility there is. 

Do DSCR loans qualify if purchasing through 1031 w/debt-carry-forward requirements?

FHA now allows us to count rental income from an ADU (additional dwelling unit) to help borrowers qualify.

That does not require employment or job seasoning instead it uses the rents to qualify and you can take out up to 80% LTV cash.Use the cash to put down on the next 1-2 or more properties as long as the other properties are debt servicing themselves it opens up more opportuities to buy more future assets and increase your passice income.  

Quote from @Rick Im: Quote from @Ashish Acharya: @Rick Im Inspection fees for unsuccessful deals and mileage for property viewings before acquiring your first rental CANNOT qualify as start-up expenses.

Also find a good lender that is well versed in STR/MTR loans to make sure you qualify for financing (if you need it) and that they can execute the loan smoothly

If you are unsure, go with the first applicant who qualified.