We found that by more or less falling on our sword and saying, "Hey, we want you guys happy... tell us what you need from us" they were more than helpful and once we had contractors they liked on board the process went perfectly smoothly.I don't live near you so can't help with your locale... but hopefully some of it helps!

My thoughts would be to discuss it first with the township, then have a qualified investment savvy realtor tour the home, get you a CMA on the current property and ARV to compare.

The program is designed to assist low-income families, and these benchmarks might exclude a lot of qualified people.That said, the requirement for stable rental and work history is reasonable, but you might consider relaxing the credit score or income requirements since Section 8 guarantees a portion of the rent.

If you go that route, ensure to use a Qualified Intermediary to handle the sale/purchase otherwise there will be no 1031 exchange. 

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

If your brother is looking to invest in real estate largely from a tax reduction standpoint they should pay a qualified real estate tax strategist to review their specific situation and what may or may not work for them. 

So I require skin in the game (average is 5% to 15%) to offset this.

For example we pay our own income taxes, broker splits and all of our other expenses directly out of what we make including required E&O insurance, MLS dues, licensing fees, Board of Realtor dues, continuing education costs, marketing, advertising, office fees/rent, transaction coordinator/ assistant fees, health insurance, car insurance and maintenance, gas, tires, software, retirement fund, etc.We are not W2 employees with payroll taxes already taken out of our paychecks, company-paid health insurance and matching retirement account plus a guarantee of at least 40 hours paid work per week, sick pay, paid vacation… none of that.So if you’re thinking you’ll be able to pay an hourly wage typical of a W2 hourly employee like $50-85/hr… that’s definitely not going to work.

If you're considering house hacking a multi family property, some lenders might be able to factor in potential rental income to help you qualify.

Seems the simple answer, is that yes, if you have a positive qualifying income you are good.