The rental market is hot right now so it probably wont matter, but in normal times, I like to pay a bit extra to get a 2-tone paint (tan/white trim) to make the unit stand out a bit, but again, just preference - I don't think either get you more in rent. 

Under normal circumstances, I’d do the cash out refi, but I’m tempted to suggest getting this larger line of credit and maybe investing in a cheaper market and seeing if you can pick up some better deals by offering cash, then refinancing out of those instead.

My friend and I are buying a condo in Salt Lake (Honolulu, not Utah) with 11 years of owner financing at terms we can make cash flow with a balloon at the end because the cash-out figure wasn't going to work for the seller.The other comments are also correct - normally it is very hard to do in a primary market like Hawaii if you're using bank financing.

Most of them have specialty’s that they are really good and competitive at.I’m unsure where you are in the process but normally I advise clients to go get 1 preapproval from a reputable lender.

But I also have some student loans (~38k) and a car loan (~19k).

If you need to push a less critical date 1-2 days and you still have contingencies in place normally an email will suffice, assuming all party’s are cooperative. 

If you would normally pay $1000 for rent and with the house hack you still pay $500, you are still saving $6k/year.

A couple things to consider would be to possibly move car debt, personal loans or cc debt over to your husband (assuming you aren't joint) to loosen up your DTI.  

It's a popular loan style overseas that allows all normal banking deposits/idle funds to sit on your remaining balance and thus save interest cost.

Sometimes I come across doctors or lawyers looking to invest, but these people are normally working with real estate agents.