Asking for a 24 month term upfront will be cheaper than asking for an extension 12 months from now, and we all know it's not going to get done on time anyways, so that would be my "ask" in your shoes.

Hi George,If you have the cash to buy your next property with financing, it's not necessary to do a cash out refinance.

I have a buddy that is in mortgage but unfortunately we are not able to secure deals with his company because most buyers have better financing or cash options and this is taking me out of the game.

While each market - real estate and stock - has it's own risk/return profile, the comfort of owning a cash-flowing hard asset becomes more and more appealing when the stock market gets choppy. 

Hard to beat the 5.5% on the new construction but you will be cash flow negative.

But depending on when you bought your house and your mortgage rate, it might be possible to convert it into an STR with enough cash flow to more than cover the cost of renting another dwelling as your new primary residence. 

We both have cash reserves, my partner does have more liquidity than me being a property owner for quite sometime and having access to it's equity.

Are there cash reserves?  

Is it worth pursuing lower priced housing and rehabbing for a buy and hold in the pursuit of better cash-flow, or is it just too risky?

I want to get him to understand if our monthly payment is too high, we don't have the extra cash lying around to fix up the other unit and get it to market rents.