Often times if you are buying a property with deferred maintenance that means their expenses were lower than they should have been, and thus their pro forma expense numbers are based on faulty information.

Who can you recommend for either new installations or repairs maintenance?

After fixed expenses, the house makes about $850 net cash flow BEFORE maintenance or vacancy (so maybe 600ish after giving a future allowance).

I would rent my house but it won't cashflow as it is on a 15 year mortgage in a high end Miami neighborhood with low cap rates, but I don't want to refi it, because it is  on a 3.25% mortgage, plus there is a lot of deferred maintenance.

Can anyone offer insight to the repair / maintenance costs of leasing properties in these areas?

* Do you upcharge on maintenance?

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

However, I buy newer and higher priced SFHs with minimal maintenance needs. 

It's hard to stand out.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

I think if I could lower the expenses from maintenance this could cash flow well.