Or if you're really inclined to get it paid off, why not use the cash flow from your first rental, then you'll be killing two birds with one stone!

They are solid, respectful and have been trustworthy, so we're inclined to make it work for them, but I'm wondering if there's any clauses or lease addenda we need to add to make sure we and the property are protected. 

For instance, the loan is $50K but the property is only worth $30K, you might be inclined to pay more than say 30% of the property value since the Guaranty in this case is $22,500. 

If you and your wife are the only members of these LLCs and file a joint return, the IRS is inclined to disregard them as separate entities anyways, so my previous point about corporate tax benefits would be moot, as all activities of these LLCs would be captured on your individual tax return, not a corporate return.If you haven't done so already, it could be worthwhile to explore this with a hired tax pro so you can get into all of the details of your situation to determine what truly is most tax advantageous for you.

Underwriters will be less inclined to approve your loan if you own a single family residential property and then you try to house hack. 

So the way I see it you could take $300x.30(tax rate) and add that back to the monthly cashflow if you were so inclined (I don't think most people do).

My inclination this whole time is to get them all on the lease, make sure they pay on time, and go month to month after August. 

My inclination is to think that people tend to see you as more of a legitimate entity if you have a web presence, but I wouldn't really know in terms of wholesaling.

You can do 10 windows yourself if you are inclined to.

But if you really feel so inclined, shoot me your address and I'll send you a bill later!