What i do know is i will convert $300k to roth at an estimated 23% fed this year.  

It depends on non-SEC 8 market rents for similar properties, the utility estimate for your property, and the tenant's income.

I only have 1 month of proof of concept so I need at minimum 3 months to get a better estimation. 

What do you estimate rent at? 

In 8 years and over 20k reservations we have had 15-20 incidents I would estimate. 

I’m seeking guidance on how best to approach this situation and would appreciate your thoughts on what you would do if you were in my shoes.Here are the details: My current home loan is $242,000, and the property is estimated to be worth approximately $420,000 (± $5,000).

You can use Airdna & other STR estimator tools to get data on potential income/vacancy based on your location and property size. 

If it would help to get a more detailed estimate feel free to reach out.Documentation is rather limited, just ID, bank statement, LLC documents to start.Sometimes there are interest-only options at 30 and 40 years, generally the difference in payment fully amortized over I/O is minimal so it may not be worth it.

With investment properties, you can typically borrow up to 75% of the appraised value - significant funds if the $245,000 estimate holds.

The best way to estimate expenses is experience and knowledge of your specific asset type and market.For vacancy, that will depend on your market and the quality/desirability of your type of unit.