As a general rule of thumb if the property has a ground level commercial requirement in order to show sufficient hardship to seek a residential use change the property should be located in a location that is not conducive to commercial use i.e residential street, close but not as marketable as properties located on neighborhood's primary commercial corridor etc. 

There are some great tax strategies for short-term rentals, but very important to be aware of the personal use rules to make sure 280(A) doesn't become an issue. 

If your market has a significant number of FHA or VA loans with zero to low down payments where a buyer can't afford to pay their agent out of pocket, your sellers may end up cutting off a significant portion of the home buying market, or once they do come around to considering negotiating on BAC, they may feel deceived, and now you may lose the potential for the recurring client that will ultimately otherwise drive your seller lead acquisition cost down.For planning: In a great business, a good rule of thumb is to estimate:100% Gross Income35% Cost of Sale30% Expenses35% Profit <-- very few businesses achieve this, but we're looking at an ideal solutionAssuming a national price average of $300k and 0.6% GCI, you'd be looking at:$1,800 Gross Income$630 Cost of Sale <-- agents/ transaction coordinators$540 Expenses <-- photos/ signs/ lockboxes/ Errors & Omissions insurance/ MLS fees/ liability insurance/ tech fees/ VA admin support/ marketing to get clients for the business (this piece should be roughly 10% of revenue, which would be $54 in this case)$630k ProfitIf your business sold 1,000 of these homes a year, you would have:$1,800,000 Gross Income$630k Cost of Sale <-- agents/ transaction coordinators (you could have 5 agents handling 200 sales each at $100k incomes and TC support at scale)$540k Expenses <-- photos/ signs/ lockboxes/ Errors & Omissions insurance/ MLS fees/ liability insurance/ tech fees/ VA admin support/ marketing to get clients for the business (you're going to est $125k in runner fees alone for signs; $25k+ in signs, $54k in ads to attract clients, $200k in photos, $10-20k minimum in E&O, $2k in liability, and what tech/ VA support)$630k Profit Scale costs will include hiring a managing broker for compliance to help oversee all of these transactions and implement legal changes and training.

I was on a Senate Steering committee way back in 85 on how to deal with all the platted antiquated lots in CA. there are millions lots created before the modern rules and these lots exist today but many are not buildable and are traded back and forth from tax sale buyers to retail buyers who dont realize their 5k lot in CA is non buildable.So there was a big conference in FT.

If you're dealing with an early 1900s home this should be a serious consideration in addition to the above.For the rest of the scope, the same rule applies.

On the surface, it appears to be a straightforward role, but it becomes far more challenging when faced with issues like non-paying tenants requiring eviction or broken systems that haven't been properly followed.As a self-managing property owner, it is absolutely doable—but success depends on treating it like a business.

But when you can qualify and deal with the process before then - usually worth it to do bank options like this until you hit the scaling point (could be 3 rentals could be 5, could be 10 etc - no real "hard and fast rule") 

They have a ~15 page PDF that describes the rules. 

Generally there is consensus that DSCR Lenders can only offer a 1% prepayment penalty for up to 3 years in MI, but some lenders have recently reportedly been flaunting this rule - I would just tread carefully here in this area, generally not advisable to get potentially tangled up in a flawed legal doc with a non-sophisticated or fly by night lender

While it doesn't meet the 1% rule it's in a stable, desirable area that'll perform more consistently for you over time so it's worth the tradeoff in my opinion.