Are there any good resources online to be able to get an idea of average monthly/yearly expenses like utilities, etc. for a given zip or city?

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.

Thank for your help Connect with a great property manager or use one of the free online tools to estimate rents.

Estimated about $25,000 including utility hookups.  

Yes, estimated about $30-35K in repairs and negotiated that into the purchase price as best as I could. 

I'm getting a contractor/ structural engineer to come by and help me draw estimates and understand how serious these issues are.

If the rate is reasonable then it may make sense to try to save fast to get to the 3.5% down payment on a double or triple - househacking may allow you to increase your savings rate and pay down that loan even faster.As for estimating costs, closing in NY factor at least 1% of the mortgage amount for tax, plus $1500-2000 for lawyer, title and fees, then the amount required by the bank for escrow will depend on the actual property taxes and insurance.