I would pretty much exhaust all my cash with a cash purchase but would have a house worth at least 55-65k.Or, do I use less of my cash to buy a 70k rental that needs less work?

After owning them for 5 to 7 years, we made the move to sell, and did a 1031 exchange into an 18 unit property that I found after an exhaustive search in the same town.  

What I would like to do is to change this to exhaust outside.  

If I help my landlord with simple maintenance, caulking, fixing can light fixtures, replacing an exhaust fan, can I deduct on my taxes the material costs and or labor since I performed this work for a rental property I do not own?

I checked the forums, but couldn't find an exhaustive resource for legal requirements.

After you have exhausted conventional mortgages ( or in between loan availability) you start looking for PML and owner financing for long term loans.  

That type of policy provides an additional layer of Liability coverage (usually in $1,000,000 increments) that start if the primary policy's Liability limit for the location gets exhausted by a claim. 

It is exciting, risky, and exhausting but the rewards can be limitless.   

Various ways and databases to look in to find claims history.I dont work a lot on the commercial side, however know the underwriting guidelines are a bit more exhaustive vs a typical residential policy.As Chante stated, make sure the incident was a covered loss, and keep in mind if it hailed more than once, or there was a wind storm one month, tree branch fell the following week, then a hail storm 2 weeks later all in the same summer - those are 3 separate claims/events.  

MD to SC to CT is one hell of an exhausting drive for a 24 hour period :-).