In terms of purchasing, I agree that having to pay all cash for property is a deterrent.

The complexity of analyzing these types of deals makes it much harder to brainstorm in terms of numbers.

In terms of the tenant's lease, I would recommend getting them to sign one of yours.

In terms of the deal finding, start networking with other RE investors in your target market.

An idea how a 1 bdrm in both these places would compare in terms of Airbnb performance ?

That would mean something like, if we get 440k for 5 properties, we would pay back 600k over 15 years, at 40k a year (some of the NOI would be held alongside the initial buffer for emergencies until a certain threshold is reached, after which excess of that could be returned toward repayment).While this is an excessively long term investment in terms of real estate not going into a funder's direct portfolio, am I missing something crucial in my calculations or expectations of realized returns that would prevent me from finding someone willing to make this type of deal?

I’m new to this and it’s not the easiest to determine what a property will need in terms of repair.

I'll never use this lender again, so I'm not super worried about maintaining the relationship, but I do think that switching to another lender now would not yield better results in terms of rate or fee, but would push us to miss our closing date and the seller would likely back out and take my earnest money, as I think they've had other interest.  

That said, I'm considering different salaried positions in the real estate industry in my market.I wanted to see if anyone else has gone through a similar situation or has any thoughts in terms of both of us being commission-based, and if that would hurt our chances of being able to get a loan.  

But at age 50, I still have about $650k in term life, which tapers off to $100k by the time I’m 65.