I only do this if I have time, I like the tenants, and only verbally.I've found the only tenants who ask are the ones who know they're losing money.

So there is a high likelihood that going in with mortgage contingency will result in losing the deal. 

Win some, lose some. 

He’s rather not lose time and add debt making improvements on our own - he’s willing to pay for the work to be done, even if 10k’s of the purchase price and pure profit for the seller.

You don’t think you’d lose $100’s of thousands not being able to sell each house separately?

@Bryan LaIf they have a lease agreement in place and are not month to month then you are stuck with the lease terms.If you plan to double the rent you'll lose the tenants, may not be a bad idea as you are looking to rehab.Legal considerations...

Since I never own a house, I don't want to lose out on first home incentive,  and the new house I want to lease not own!

Get the most mileage you can out of this + a blog and then when you are at a tipping point or losing proven business because of your lack of a fully spun website, jump to one of the big hosting and design companies.

I don't want to get ourselves into something that cost us to lose money to start, when starting small would have sufficed. 

I’ve had dark dreams about losing it all, and having to crawl before a new boss.