If the lender is asking for only 12 months insurance, you will have zero months insurance in escrow after closing.Taxes are more complicated. 

So it's complicated.

Really a book of information can be written about infill development in LA, it can be a very complicated, tedious and risky project without someone knowledgeable about LA  development on board. 

The person who does this refinance will also already have what she/he needs to do the mortgage on your next purchase, for the most part, and will be able to allow you to write more aggressive offers than would normally be possible for someone with finances as complicated as yours.

If you had a general contractor doing work on a draw basis, you could minimize the amount of check by having that contractor paid once or twice during the entire rehab process, instead of individually paying for each project/sub-contractor.Such a JV with IRA's belonging to disqualified parties is a complicated ordeal, and not something we would generally recommend.  

This is going to be long and complicated, and I hope I can go into depth without causing confusion.My dad passed away last April and left me his home. 

I get that it's complicated and depends on my situation.

This argument seems valid to me, given the cost and time I would be committing to buy all of 2 houses, and the fact that it complicates a process I am already struggling to tackle.

If this is single family residential the actually layout isn't especially complicated, but for a multi-family it may be required to meet ada clearances.  

It is a complicated space but you can easily get into it by investing with people who have been doing it for a long time.