The previous owner made a really poor elaborated lease that looks like it is going to end in April 2025.

Is it a poor plan or are there any obstacles I may be overlooking?

Picking a house with major, costly structural issues or in a location with poor rental demand can hurt both the rental and refinance phases.

I understand wanting to save money on the monthly fees, but when it comes to maintaining an investment that can very easily be devalued by deferred or poor maintenance it's worth it. 

Great on paper, poor in reality. 

I want to buy a place just north in the Seirra valley poor mans tahoe :)

Insurance companies will likely not pay a claim from the roof or subsequent water damage because they will know the roof is already in poor condition.

If you recall also those with swimming pools in Los Altos hills that were on a hillside some of them the water came out and flooded into their homes.. it was quite random.. my kids were walking home from grade school alone ( Back in those days it was OK for kids to walk a few blocks by themselves.. )  The poor folks though on Hwy 17 connector through Oakland got pretty much squished when the top deck fell down that was very sad..

Them damn poors hate working.

Professional tenants target mom and pop landlords with poor screening processes...rather than large class A and B properties with professional screening processes that disqualify most problem applicants...and lots of neighbors who actually pay their bills.