It's a little different investing there as older homes (these are 100+ years old) can bring on a lot more expenses than normal.

That takes time and effort and expenses for due diligence that should be set off by the sale price and I doubt he will look at it that way.You'll get a better deal by making an offer on the whole mess, not cherry picking.Are these to flip or hold, determine that on each property. 

He does exceptional work and is always the lease expensive of the bids I get

Many investors seem to take the approach that a PM is just an unnecessary added expense that they can handle themselves, but I know from experience that a great PM will usually rent your property more often, for more money...not to mention take the daily management grind off the owner's plate...freeing them up to do more deals!  

If we were to get into this and find out we did not enjoy being landlords, at least we would be able to offset our monthly living expenses along the way.  

It seems I might be 'self dealing', but if I kept all income and expenses in the same initial ratio, is that the same as how I have read you can 'partner' your own cash with a SDIRA?

Unit 2: 2 bed, 1 bath Rent: $700 per monthUnit 3: 1 bed, 1 bath Rent: $625 per monthUsing the 50% expense rule with the calculator it stated that this should cash flow $460 per month. 

and can a Roth IRA be rolled into the Roth version of the SD-401KI too have a SDIRA and last year filed a 990-T and overall the taxes came out to just above 10% paid on the income after deducting all the expenses

Maybe I need to educate myself better to gain more confidence, but it seems to be the least forgiving on a misstep especially in an expensive and competitive market like San Diego...

Lots of people wanting me to pedal expensive "get rich quick" investment educational programs on their behalf.