Also consider that flips are also taxed at ordinary income, which can provide tax challenges as well.I would echo what others are stating and make sure you speak with a tax accountant, as this seems like tax sensitive  situation you are going for

Time-Sensitive Closings2.

to me your being to overly sensitive on this matter.

The HELOC analogy is very helpful.Those up-front fees/commissions, and the sensitivity of the product to finding a good agent to "design" a policy right, are big turn-offs for me. 

Remember also HELOC's have floating interest rates and you're dependent on a refi in 12 months and the fed's stated policy is to increase rates further, so you should do a sensitivity analysis on how high rates can go before the property no longer cash flows - if refi rates are 8% in 12 months, does the deal still make sense? 

Best way to underwrite these deals is to understand all the costs and potential (including what it takes to get there) along with time.Taking all of that and plugging it into a sophisticated proforma to evaluate the deal along with the risk (sensitivity analysis) to understand what the true value of the asset is.

What’s left for the small housing provider are the students who are price sensitive; and as in all industries this is not the most profitable niche.  

I joked and said yes because you should know that information to understand interest rate sensitivity.

This works OK for relatively static and simple investments like a private placement or crowdfund, but can become rather cumbersome and expensive with a more time sensitive and transaction intensive asset such as a rental property.

This has to do with the time sensitivity and complexity of the probate process.