Hang on a few more years and enjoy the very low vacancy, maintenance, and rapidly appreciating rent that comes with a condo in O4W.If you have a good tenant, then keep rent the same and don't think about the property except at renewal time.  

This has created a challenge, because:1.He cannot be on the note for the building as a rule for the self directed IRA (may be an exception if the note is non-recourse, but I can ask his plan administrator for the specifics around this).2.Conventional mortgages require evidence of the down payment for the person on the note and I don’t currently have that much in my account (although I could show enough submitted invoices to have that much in my account and might be able to get the full amount in time).Given this, I am thinking that we only have a couple of options:1.A non-conventional loan. 

.+ $8000 closing costs (that's what it would be here, I realize this is very state-specific)$259,000 all in on an exceptionally modest rehab.Lets assume that actually gets you to $285,000 (which is a not great assumption.)$285,000 - $259,000 = $26,000Now your flipper needs to sell it.  

With the exception of some overlays by a lender, there are few deviations from Fannie underwriting guidelines.

Originally posted by @Steve Babiak:An entity can never take advantage of the IRS Section 121 exclusion on capital gains.  ...except for eligible single-owner, disregarded entities (like a single-member LLC).

Yes, those are all "asking prices," but they are in the ball park (there are always exceptions) of what the properties should sell for. 

Exceptions are historical neighborhoods that are in high demand.  

There was one house that sold at the zillow estimate recently, but this seems to be the exception rather thatn the norm.

If you elect to be taxed as a sole proprietorship it does not remove LLC protection, except that a sole ownership is harder to avoid "piercing the veil" through alter-ego.

For existing lien, you do not have to wait for any period.With small banks or mortgage brokers; they are flexible and can have exceptions based on your assets, credit score and rental income.