My wife and I rolled a $60k downpayment 21 years ago into current equity around $4m today.

I am most interested in Multi Family properties and I am currently looking for my first deal to get things rolling. 

Its a rolled on rubber flat roof.

And guess what, he was given a cease and desist order, shutting down his business until he had a new location where he could legal run the business. 

At this point I am managing with spreadsheets for each property, rent rolls, and calculations on returns.

If the rolls were reversed, you should want to do exactly the same thing as well. 

No standard rent roll or P&L.

I would probably roll the dice on an 80s house in CT, even if the looks are a mess, the rest should be fixable/straight forward.Getting it on the market before he holidays would be good.

Think of a mechanic that is telling you to buy Car Model A over Car Model B... they are the ones in a position to know that Car Model B breaks down all the time, based on what they see rolling (or being towed) into their shop. 

., former employer 401k) to a solo 401k are not reported on Form 5498, but rather on Form 5500-EZ, but only if the air market value of the solo 401k exceeds $250K as of the end of the plan year (generally 12/31);When funds are rolled over or transferred from an IRA or 401k to a self-directed IRA, the amount deposited into the self-directed IRA is reported on Form 5498 by the receiving self-directed IRA custodian by May of the year following the rollover/transfer.Rollovers (provided the 60 day rollover window is satisfied) from an IRA to a Solo 401k or self-directed IRA are reported on lines 15a and 15b of Form 1040;Pre-tax IRA contributions on reported on line 32 of Form 1040;Pre-tax solo 401k contributions are reported on line 28 of Form 1040;Roth solo 401k funds are subject to RMDs;A Roth 401k may be transferred to a Roth IRA (Note that from a planning perspective, it may be advantageous to transfer Roth Solo 401k funds to a Roth IRA before turning age 70 ½ in order to escape the Roth RMD requirement applicable to Roth 401k contributions including Roth Solo 401k contributions and earnings.)