Ive had this rental for 10 years, its a single family, 1b/1b, built in 1920Its almost paid off (I owe 2K on mortgage)Bought in 2019 for 25K, now its worth probably anywhere from 40K-80K ( zillow says 80, realtor says 40K)Market value rent is $475-500Ive been renting it for $200...( insurance 15$ per month and taxes 60$ per month)Expenses over 10 years: I put new shingles over the roof two years ago (2K), then water heater fix $150, foundation fix $200, plumbing (main line plugged $200 one month ago, and then a week ago it happened again so another $200) This year I will need to paint it, so I am getting 1K quotes...Need to tell you that when it rains the water gets into the basement, but its been like that for 100 years since it was built 1) Would you sell it? 

.#3 Contact Local Contractors for PricingCall local Subcontractors and get budget pricing for common repairs on your typical rehab project.For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch.Note: Some contractors will be reluctant to share pricing without seeing the property, but tell them you are just looking for a rough budget number you can use on future projects.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

Lumber availability, Shingle, stone, insulation, these are materials shipped in from other countries and states and the costs between states aren't going to be that significant especially when dealing with national suppliers.

I can have everything built very cheap because he buys a lot of lumber, drywall, plumbing, shingles, and he builds all his own trusses.

I have been able to get mortgages with older roofing, with slightly curling shingles, but a newer roof is better.

I'm personally handy around houses so I used ~$6,000 and some elbow grease to repair a water damaged garage (posts, sheathing, shingles, exterior paint), upgrade to vinyl windows(entry level), painted every wall, removed nicely perfumed carpet and refurbished hardwood floors, replaced kitchen counters and appliances, installed heating duct to 2nd floor. ~2 years later insulated attic with blown in.

Other companies can have endorsements at no extra cost that extent your polity like a better shingle program...where a company actually pays you to put better shingles on your roof upon damage this is a great program and shows a company that wants the risk (your house) to be as good as possible and basically pays you more for it in the event of a loss....Nationwide has a better shingle program in some areas of the United States.  

Squirrels in attic cost me $350 for a week of trapping (came by every day to check Traps), but then they will sell you the exclusion service, where the solve the problem (construction gap) by installing metal alont the roof to gutter line (plywood does not extend all the way down and there is about a 2" gap, sometime covered bg the shingles).

Washer and Dryer. 1 Stall Garage detached.Unit 2 (Upstairs) 770 sqft. 1 Bedroom 1 BathWe split the water to the upstairs unit (submeter) and pass water/sewer costs to tenantsOriginally only one gas meter - converted the upstairs unit to all-electric to avoid the need for a second gas meter.Needed a new roof (redecking and shingles)Updated windows, new paint and trim, new garage door.

As to the why of what you're dealing with - a lot of insurance companies are doing this because roofs over 15 years of age in Florida are highly susceptible to wind damage because of the brittleness in asphalt shingles that's caused by long term sun exposure.