Together we make about 120k-ish and as were doing this, were actively paying down our credit card debt which together is about 20k at the moment, just fyi.I feel like this is a solid plan, but I'm not too big headed to admit that I don't know everything.

Quote from @Richa Wardhan: It's inside the city zoned RG-1, we would like it to be a vacation home and STR Hey, RichaIs the home already a vacation home and STR or is it a primary residence looking to convert over after potential ADU built?

We have a potential buyer of a lot in St Augustine, FL who would like to build a new single family short term rental.

So you'll be putting out quite a bit of money to do that, and when you sell, you'll most likely have to convert it back.   

I use Proper insurance, unwritten by Lloyds of London, for my STR - covers the extra issues you would expect from an STR like vandalism, alcohol liabilities, business interruption up $10k, hot-tub cooties etc.

I first like to short list based on numbers and then deep dive.

I think that it is a good long term investment with some serious upside, but don't kid yourself - your car (or your tenant's car) will likely get broken into at some point.

I have been considering asking to buy the single family in cash to separate the deal but would like that amount to be subtracted from the purchase price while keeping the cash I would spend on the down payment the same to include the single family that way the seller gets the same amount of cash upfront.

It sounds like you have a strong foundation, and getting one-on-one guidance can definitely help you learn more in taking your next step.

The additional bedroom adds to both the rental value, and significantly to the appraisal value, obviously.Given it's priced as if it's a 2 bedroom and not a 3, it seems like a great deal.