Health insurance payments, Health savings account lots of options. 

build to rent is great. they are an intermediary that help investors contract direct with turn key new build. they are pretty sophisticated we have sold a house so far and we are looking to sell other multifamily with them. there is a vetting process and as an intermediary they don't control construction they help vet builders and establish relationships. they have a big team. the other builder I've never heard of but unless you can see your house I wouldn't touch it. rent to retirement has a strict policy of 90 days until certificate of occupancy until they will send a deal out they are good at what they do and I'd recommend them. they have options all over the country and established relationships.

This could give me an option as a house flip if the numbers don't work out in my favor for positive cash flow.Target Returns:Given the higher risk, what cash-on-cash return or annualized return should I be aiming for?

The midwest has great options - Indiana, Michigan and Ohio has lots of great sub markets with good cash flow. 

If your cabinets are made out of plywood and nice enough painting is actually a great option. 

A good lender should be able to piece together a strategy with you, whether that's cross collateralizing or not, underwrite each option with conservative numbers. 

I'd like to move forward with option "b".

@Bill B.It will give rise to a new option for younger generation. 

For the most part vs focusing on a specific neighborhood or two I would say keep you options open to all. 

If it does vest, then the 2nd isn't currently $8k and the paperwork could further help your case.Other option is to completely ignore the equity in your residence and look for creative financing on the property you want to purchase.