@Cameron Tope thanks for the number on a cash flow basis.

Sell for lump sum/cash out - Seller is taxed at LT cap gains rate based on price/ property basis(?)

One other issue is that since you are stepping into his shoes, the basis for the properties remains the same, for both depreciation and cap gains when you sell.

I know the general rule is to own more than one door but does that still apply if I'm renting it out on a per room basis?

When done through the estate they receive the property tax free due to a step up in basis on Grandma's death.But that requires waiting and it sounds like there's some immediate attention needed.   

I do not believe that I personally could achieve the 1% rule on either property on a monthly basis, but annualized, the rents will likely be 8-9% of the total asking price for the properties. 

I'm thinking if it makes 100-150 per door on a conservative basis then it's a go.  

The general idea is that if a tenant caused the damage, then it is the tenant's responsibility.I would question your landlord on this fee on a case-by-case basis as appropriate.

It’s also not just that we fill out a contract, we are taking the time to look up and curate listings for you, take you for showings on an on-call basis since time is of the essence, reading disclosures and engineering reports, etc.

If you do the 1031 and purchase more than you sold then the additional purchase amount is additional depreciable basis and would give you more annual tax break.The 1031 doesn't have to be 1 for 1.