Can the property sustain itself now for what they are asking for.

Has he broken the lease or not paid in a timely manner at all?

This can only be used in a positive manner, so missing or late payments do not count against the applicant. 

It may be enough just to prune the trees prior to seasons where you might experience higher than normal windspeeds or heavy snowfall.Many times a court will try to determine if you "acted in a reasonable and prudent manner when compared to others landlords under similar circumstances". 

And any suggestions on strategies for getting the repairs done in a timely, cost effective manner.

Even if the grout is sealed, the tenants do not care enough to clean the mess in a timely manner, the stuff in it will stain the grout and with the chemicals and pressure wash the seal will fade/go away.  

Given how crazy the market's been recently i do not think the craze will sustain over a long period and if the market cools down in some areas it makes sense to invest in a property that retains its rental value.Based on initial research, it seems like Charlotte fits the criteria as it has seen decent population growth and appreciation in the recent years and is my first choice but I haven't had any luck finding properties that checks the boxes. 

Hi Brian,Make sure zoning allows a 4 plex.Make sure you have enough Amperage at the drop for another family.Make sure you have the amount of parking you want to offer the market.Make sure you have enough water coming in for 4, especially if it used to be a 1.Make sure you don't downsize the 4 rental sq ft to be worst in the market vs having a very marketable 3 plex (re sq feet).Make sure you do not trigger any added fire code things, such as requiring a fire escape or fire suppression systems, etc...Find out If you will be required to now have a dumpster as a 4 plex, and where will it go.Find out if the remodel will trigger any grandfathered items to be delt with, ei bring wiring to 2021 code for entire building, ditto heating and building thermal requirements, etc...Find out if the lender is "On Board" with you "Restyling the Asset" in this manner they are lending on.A 3 to a 4 is bigger scope job than putting in a new kitchen, and the lender may not consider it re-hab, meaning it might be to them, construction, and not allowed on the loan type you are seeking.Good Luck!

This need not be complicated or full of legal mumbo-jumbo:"Dear Tenant, you were provided an opportunity to renew your lease and have failed to respond in a timely manner. 

I also don't know what kind of profit they should expect in being a lender in that manner.