Don't look for lowest rate, look for lowest cost on fees as you will either refinance out of that loan or sell- the prepay will hit you on the back of the head like a cinderblock wall.

Hey @Brett Baker, generally, any place with a great water view or directly on the water will bring more revenue.Of course profitability will all be based on purchase price and prevailing nightly rates in the area.If you find a cool 2/2 or 3/2 right on the water with a great view for 1.5m or a 2/2 or 3/2 house a block away for 600k, then I would look at the house over the condo.

So, what is happening today is not as important as what will happen in the foreseeable future.If rents are increasing faster than inflation (I use 5% per year as an average rate), then it may be worth holding the property, since your cash flow will increase as rents rise.However, in your post you stated, "Mortgage rates have kept increasing as well, that's why I put a range on negative cash flow."

HOA will eat up a lot of your money. 

If you don't have appreciation capex will wipe out your cash flow. 

While it will not reduce the actual cost it will help with the monthly cash flow.I am curious if this was a single-family house converted into a double.

It will teach you so much, has the best financing options, least amount of risk, and will let you know if you want to be in this business or not. 

I have a cosigner willing to help, but Im unsure whether they must be in my LLC or can just be a guarantor, has anyone dealt with this before?

I understand that not every project will be a success, and I am okay with that.However, when it comes to financial wins, which option do you think offers a better financial outcome?

Is it doable - yes but you will need to go to a lender who probably uses their own funds vs. an instituational lender as they will not like 2nd position nor the low amount.