Good Day,I need to estimate how much the insurance will be before I purchase the property. 

I'd be curious to know what the property management estimated your year 1, year 2, and year 3 revenues to be. 

The property manager had someone go out and give an estimate for around 11k to replace the entire roof.

I pushed back on this and requested a re-appraisal - I submitted comps showing what other less desirable condos in my area have recently sold for - but the appraiser is sticking to his estimate (of course he's not going to admit he made a mistake).

The property will be available to view early next week (after the holiday weekend) for estimates for the job.If you know of any solid, reliable general contractors who work on rental investment properties . . . your recommendation would be greatly appreciated!

I have been able to find deals in the current market using the BP calculator that fit my buy box, but when I see that homes in that area are estimated to be ~30% overpriced and am watching in real time prices drop it leaves me unsure what to do.

Have you already used a source to estimate the STR income?  

The property is now valuing minimum at 365K via Zillow, HAR, and in the 400's with CreditKarma, with identical / neighboring units selling +$20,000.00 more than those estimates. 

I did my best to estimate all of my costs. 

Some lenders are going to want 2-6 months of lease history before lending, others can lend with just a market-rent estimate, others don't even need to show positive cashflow.Ultimately every borrower is unique, every property is unique, and therefore every transaction is unique.