His future was already 'blown' in many opinions before he even got started, but he's built himself a pretty solid existence from the ashes. 

If it becomes more frequent (a few times a month/weekly) I would find a solid "handyman".

And without the risk associated with borrowing for fixed assets on your own.There's no real downside to this equation as long as the DSTs are solid and your focus for growth is on the cash side. 

Don't waste the time, just serve the 60 day notice and if they are still there after 61 days, have an attorney file an unlawful detainer suit against the tenant.

My was new construction and cash flowed pretty solid from the beginning.

By trying to do everything at the same time, you will end up going nowhere and wasting valuable time, money and efforts. 

Although I may lose the deal if I force his hand this morning, I will at least stop wasting another weekend on the MLS with it marked pending.

Seriously, within 4-5 years, you could really be set up pretty solid.  

They had a solid plan to finance everything through the LLCs (using 5 yr/ 30 y AMM loans).Could you walk us through your perceived benefits of putting the homes in LLC's while you're still small?

Trying to finance land in the northern counties without some collateral substitution is, IMO, a waste of time.