The property has had little to no maintenance and it's in a decent neighborhood with mostly homeowners. 

Think lenders, insurance carriers, property management, contractors, etc.

Check into insurance and tax rates in the areas, along with estimated mortgage costs. 

.- Insurance: Short-term rental insurance (beyond renters') can protect you from guest-related risks.- Licensing or Permits: Check if your area requires permits, as some cities have fees for short-term rental operators.Breakeven Analysis: To calculate your breakeven occupancy rate, add all monthly expenses (rent, utilities, cleaning, insurance, etc.).

These items can make it expensive or difficult to get insurance for as well. 

Carrying costs in purchase and or rehab is financed, cost of capital on refi, re-recording, title, updated insurance, etc. their are many costs at play after initial funding then to transition long term unless your straight cash on the front end.

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

It also depends on the situation sometimes a HELOC is warranted for short term financial needs so long as you have a plan to get back in the same or better financial position afterwards and the "means," and "will," to carry out this financial or mortgage plan- HELOC's are typically full documentation qualifying loans so you'll need actual income to qualify whether it be from pension, insurance, rental's, etc that are all fully documented on taxes, W2's, 1099 forms, etc.

What are the best companies to sign up your properties with for insurance housing placements?

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.