My suggestion with you would be to raise capital or focus on marketing for off market deals (yes, I'm a broker telling you not to buy from me).

I would also recommend doing a pre move- in inspection with the tenant, as well as taking pictures of the property, that they will sign off on- so you are both on the same page of the initial property condition- so if there is damage when they move out, they can't say "that was there when I moved in" because you will have proof.

I’m interested in wholesaling & subject to start off than would like to transition into house hacking, short-term rental etc. 

I would look into these guys https://www.submetersolutions.com/If that doesn't work, just split the usage based off square footage and charge the tenants in proportion to that - not 100%  accurate but good enough.

In my area the amount of inventory has had a high impact on off season bookings, with a tremendous amount of price pressure chasing bookings.

You noted your water retention is off site, so that gives you more buildable space. 

A current tenant has damaged the rental property beyond the normal wear & tear. (3 by 6-foot hole in dry wall; Garage access door complete broken off with damage door frame, the main entrance door way frame is broken and need to be replace, damage to the rear entrance door frame as well).

Lots of one off new builds.   

Purchase price: $270,000 Cash invested: $100,000 We recently closed a successful investment deal on a duplex that we acquired off-market through a strong relationship with one of the largest investors in our town.

Most banks hire 3rd party asset management companies handle the sale, so if you call the bank they will just pass you off - that will be after being tossed around from department to department for two hours.