I only have student loan debtI have a full-time remote jobI have no prior experience in real estate investingMy credit score is high 700'sHere are the details about the property in Zenda,WI:Asking price: $235KIt’s being sold by out-of-state heirsIt needs at least $50K in repairs and updatesThe neighboring house recently sold for $235K (though I don’t have details on its condition before the sale)A family friend who owns a construction company assessed the property and noted the following:Replacement Needed: Furnace, Water Heater, Water Softener, Floor (concrete replacement needed due to unevenness), Roof, GuttersUpdates Needed: 1.5 BathroomsConcerns: Black mold and water leak marks upstairsRemodel Suggestion: The staircase is very steep and narrow; recommended to relocate and extend it into the living spaceAdditional Work: The property slopes downward, allowing rain to flow into the house.

I have a tenant whose condo suffered a major roof leak, which caused internal dry wall and related damage.

Bring an air compressor with fittings, hook it up, go around listening for air leaks.

The hard part will be finding the leak in that case.

Have a 1960s 30 unit single story motel where we are coming up on some end of life issues: the cast iron plumbing is disintegrating underneath bathrooms, radiators are starting to leak, electrical is in poor condition, and just today, discovered significant termite damage affecting multiple rooms.

What about the plumber that stops a flooding leak on a Sunday morning or the HVAC tech that fixes a furnace under a crawl space in the middle of a freezing night?

Quote from @James Nix: It's obviously a leak and the most likely culprit is the toilet.

Any company insuring your properties without an inspection most likely has a clause buried deep in their policy allowing them to deny claims for conditions found on the property that do not meet their UW standards and they will deny you claim based on "the house should have not been insured with them anyway".Although the inspections can be annoying look at it from the other side.You pay them 1000 to 3000 a year to insure a rental property where they agree to pay out possibly hundreds of thousands of dollars if it burns down or up to 1 million if a tenant slips on a bananna peel and falls down the steps or the tenants dog bites someone and since you didn't enforce the tenant having their own renters policy to cover the dog bite the landlord's policy is paying out.The insurance company is very much like your rich uncle backing your business venture - you run the business, he takes on the financial risk from disasters, and doesn't even get a say in who lives in the property.Your rich uncle asking you to fix the steps, put up a handrail, etc which is in your and his best interest long term.Do you really want to rent out a property with a busted front step and a bad roof that is going to leak sooner than later?

Update: I just had one of my mini splits leak into an interior wall creating some damage to my awesome 1912 Craftsman.

It depends on the State and the County, just google "real estate photos with iPhone" and you can find a bunch of services.