I am sure with many investors it isn't unusual to have dealt with this before.

Seal coating the driveway should be about $500 (unless you have an unusually long driveway)... so unless you need a lot of carpeting, that $5,800 estimate seems a little high for a lower end rental. 

Filing a lien or going after someone's bond is another very slow and uncertain way to recover payment.I'm sure an experienced contractor could match any investor scar for scar.   

Or nothing and that would be unusual.

If your duplex is in Montana, then yeah, two Florida applicants is unusual.

I suppose it's possible the water is just trapped in the basement but it would be unusual that hydrostatic pressure couldn't just push it out of any crack or seam in the basement between the walls and floor or through wall joints/cracks.

-Since the future is so uncertain, I'd try and find a tenant whose employment may not be effected during this time. 

MF go from 10k per unit to 50k just in the last 5 years even in EAST Cleveland  All the best  With all due respect, you are ignoring 1) data from multiple reliable sources.  2) the fact that what you have seen is not unusual in other markets which is why neighborhood scout shows Cleveland’s 10 year appreciation to be just above the average for large cities. 3) that the long term Cleveland appreciation is pathetic (1 out for of 10 for this century per NeighborhoodScout and significantly less than 2% annual for the century and less than the inflation rate) 4) that Cleveland’s population has been declining at least 50 years and is down ~50%.What you have is a severe case of confirmation bias. 

This isn't an unusual request.

unusually those who bring more to the deal or have more experience are able to negotiate a higher profit percentage from the partnership.A Lot of partnerships where people bring in money want more money from the deal in the earlier years of the partnership so they can re-coop their capital and are willing to take less once their capital is fully paid off.You want to make sure everything is in writing when you meet with the attorney.