Most likely the issue is poor surface water management, failing gutters or missing downspout extensions.

@John Mason Assuming you are in a decent part of town, you should have no issue with demand for a medium term rental.

I immediately see repair, permit, and maintenance issues.

Looking for lenders who you've seen are willing to issue a HELOC (or loan) in 2nd position on an investment property. 

Banks requires (2) months copies of your checking or account for the down payment.If you get the cash into the account 3 months prior it will "not" show as a large deposit that you have to source and show it came from a personal loan which then causes no issues in underwriting.

What else can i ask just to prevent potential issues with a tenant.  

Title companies have been reluctant to participate, however, we just closed a loan in Texas where the borrower signed remotely using a remote notarizatiion service and the title company accepted this and issue a title policy. 2.

Common examples: Is there a maintenance charge with every call/issue? 

The biggest issue with using all cash is that it ties all your money up and denies you the leveraging power of using the banks money.  

.$995 is great rent but you also don't want to evict if tenants can't pay because turnover costs can kill the ROI.Just my opinion  Looking back, I think a cheaper entry point could have been negotiated, but this one was my first ever purchase and I really wanted something to get my feet wet with. i think the emotional satisifcation of having a first rental was well worth a slight overpay.