However, if you already know there’s going to be a lot of deferred maintenance,then it would be wiser to fix the deferred maintenance then hire a property manager so you will get less future headaches.

As long as the value of the portion used as rental (2/3rds of the triplex) is equal to or great than the value of the investment property he sold he would defer all tax on his sale. 

Usually a payoff is just the remaining principal balance plus interest accrued to the date of payoff, in addition to any other small recording or miscellaneous fees.Are they tacking on deferred interest from 10 years ago?

-is there any preventative and/or deferred maintenance I need to be aware of (i.e.; HVAC, water heater, roof, flooring)The owner requires a letter of intent to buy before it can be showed.

They were purchased having been rehabbed in the prior years and with no major deferred maintenance.Essentially going into the 2017 year the portfolio represents a group of houses that have 3 or 4 years of “wear” on them after a rehab process.The results were as follows (by Property) PROPERTY INCOME Eastpointe 2 $10,838 Royal Oak CT $10,800 Eastpointe 3 $12,660 Eastpointe 4 $11,401 Eastpointe 1 $10,620 Total Property Income $56,319 PROPERTY EXPENSES Eastpointe 2 $6,366 Royal Oak CT $6,475 Eastpointe 3 $6,867 Eastpointe 4 $7,061 Eastpointe 1 $5,587 Total Property Expenses $32,357 NET PROPERTY INCOME Eastpointe 2 $4,472 Royal Oak CT $4,325 Eastpointe 3 $5,793 Eastpointe 4 $4,340 Eastpointe 1 $5,033 Net Property Income $23,962 Alternatively here is the result by expense type (and compared to budget): Budget Actual Actual to budget Net Revenue $48,400 $56,319 $7,919 Management Fees $5,280 $6,636 -$1,356 Insurance $2,958 $3,939 -$981 Taxes $9,486 $12,092 -$2,605 Repairs, inspections $9,000 $7,255 $1,745 Utilities, Legal Fees, Other $- $2,435 -$2,435 Profit $21,676 $23,962 $2,286 Finally, here is an average breakdown per dwelling: Per Annum Per Month Management fees $1,327 $111 Insurance $788 $66 Taxes $2,418 $202 Repairs, inspections $1,451 $121 Utilities, Legal Fees, Other $487 $41 Profit $4,792 $399 A couple of points re the above numbers:-We had nil vacancy over the 2017 year.We also had some back rent which got paid.

You don't want to pick up the bill for someone else's deferred maintenance or contested title.

What deferred maintenance is there?

@Josiah Collins, You're certainly on the right track thinking about a 1031 so you can defer tax on the gain of the SJ house. 

Househacking is great because as it provides you the opportunity to get into real estate with less cash down(3.5% if you did an FHA).It also provides you "training wheel's" to becoming a landlord as Brandon Turner would say.A lot of NY real estate investors are investing in upstate NY, nearby states such as CT, NJ, PA or doing long-distance investing in states across the United States.Not many NYers are investing in NYC itself because of the higher entry point and a lot of the properties do not provide cash-flow opportunities(however they can provide appreciation...but not many investors like that speculation portion).Remember from a tax perspective that your househack is part rental property part personal residence.The personal residence portion of the house is eligible for exclusion of upto $500,000 of gain if you live there for 2 years.The investment property portion of the house is eligible for like kind exchange upon sale deferring your gain.Also you are able to deduct direct expenses and indirect expenses related to the investment property on your tax return.

Since you said you have an attorney I would defer to them.