Luckily my newest and largest property only took three months to complete all majors repairs and for bookings to start filling up consistently.Do you have a mortgage?

The investment consists of three building, 2x 3-familty units and 1x 4-family unit. 2 units need rehabs when current tenants move out.

Residents must settle overdue rent before moving.The Section 8 housing voucher waiting list is closed, with a wait time of three to five years, but Dosker Manor residents are being moved to the top of the list.LMHA has 2,800 apartments citywide, with 1,500 past due on rent, but no evictions for non-payment in four years.

New York City allows members of the public to have roommates in both single-family homes and in apartments, provided that these roommates maintain what is known as a 'common household,' meaning they share the livable space of the dwelling unit," Under the NYC Administrative Code, no more than three unrelated roommates can occupy a dwelling unit and maintain a common household, which means you can take on one or two roommates.

I've seen this happen three times on large portfolios with a lot of equity.

Each software I look into claims to have all three attributes (property, bookkeeping, project).

Just because you don’t have the money to repair, does not mean that a tenant needs to endure someone coming out three four times to repair something that seems it’s unrepairable and problem needs to be replaced. 

Three out of four of the worst houses on the block (including mine) have all been sold and renovated in the past 6-8 months.. and the 4th was just foreclosed on, bank did minor fixes and are putting it up for sale.

Should I have the agent send three separate offers, or is it more effective to choose one offer and include a letter that outlines the other options?

Make sure to do sufficient market research prior to jumping in...especially if you are considering STRs.