Even if you have to file an extension.  

I guess in the two instances I laid out, not sure what a lender's opinion would matter.

It's not nearly as extensive as it would be to make-ready for a new tenant, but sometimes there are items that need handling  (that the tenant hasn't mentioned previously, for example) to keep the property in good working order and keep our long-term maintenance costs down, so the $500 renewal fee is also meant to cover those itemsAt the end of the day, we make far less on a tenant renewal than we would on a new tenant - but keeping solid tenants in place keeps costs down for us and for our investors, so we really push to keep the tenants we have whenever possible, and that costs money.

Considering that the tax filing deadline is in a couple days, my personal opinion is that you should pay the amount you believe you owe and then take an automatic extension.  

I am based in California, not entirely sure if it's legal to ask them to fill out forms as extensive like this one.

@Chiagozie Fawole 90 days that included a 15 day extension as my lender wasn't ready to close. 

It helps that most of the threats to be sued have no merit which I think applies to your situation (good lawyer would let you know).Fix your insurance issue and get a good lawyer to assist you in this instance if your insurance does not provide one.Good luck

Whole life insurance is an interesting thing....do extensive research and make sure you understand it 200% before jumping in.Best of luck!

There is extensive discussion on this topic on the DelREIA facebook group.

For instance:1) HOA Fees2) Insurance on the property3) Mileage on trips to the property4) Repairs5) Property Taxes6) DepreciationAs far as depreciation, I'd recommend getting someone with real estate experience to prepare your taxes the first year after you convert your property into a rental.