If you have a 2 bedroom and you typically get $600-700/month depending on your market, and you can get $400/each bedroom, you are already ahead of the game and could have a non-stop influx of tenancy.

There is no straight path that I can find.  

If a cash offer gets the deal done, and it cash flows, you are still ahead either way, but you are underutilizing your windfall in this scenario. 

After making 15+ offers and getting no bites, we were filled with self-doubt and wondered "what the heck is wrong with this house" for a while but decided to forge ahead.

You could be ahead of your time with this idea but the expense could only be justified in the metropolis of NYC or your CA.

Hope I’m not getting ahead of myself.

Our prices year over year are up, and even without filling those gaps we are already ahead of last year. 

Thanks for the detail on lessons learned, I will keep in mind not paying contractors ahead of time.

I am currently a personal guarantor on all of them excluding the Freddie Mac loan and would love to lower my personal reliability.I guess the point becomes is it better to save up that money in liquid (aka after-tax) vanguard accounts and then bulk pay off down the line or to just put it straight towards the loan.

Then, if you didn't create a partnership to hold the property, then it straight onto your personal tax returns and you each report your percent interest on the property.