@Ali HamadeSince your property is ideal for house hacking and generating rental income, targeting an investor-friendly audience is a smart approach.

I'll be 45 next month.option A) Kiyosaki Model: Don't sell and run either long term or short term rentals through it for a year to show income on the property than pull a $300k mortgage on it to build another house in the same neighborhood... repeatoption B)  Ramsey Model, Sell it for $600k.

Rentals generate passive income, so an S-Corp offers no added tax benefit.

They will issue an IRS Form 1099 in January, reporting your total taxable income to you and the IRS.

Wife and I are both self-employed so acquiring a traditional mortgage is challenging based on our "on paper" income.

Owner-Builder Construction Loan (Challenging but Possible)Some lenders offer owner-builder loans, but they usually require:✅ Strong financials (good credit, assets, low debt-to-income)✅ A solid construction plan, budget, and timeline✅ Proof of prior experience (renovations help, but formal experience is a plus)✅ A licensed contractor or project manager to sign off on the build2.

My CPA says that I don't need to report the income any differently than I have been so this is a plus (less hassle). 

I have  a W2 job and look forward to the losses this year to offset some of my income (Not my 'WHY' for running an STR, but a nice bonus).

Find out through asking the right questions what will help solve any existing problems, that will give the seller a nice monthly Passive Income Stream, etc. 4.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.