Specifically converting a building with Class B rooming units to Class A apartments.

.- Lower down because I can do FHA loan- Probably don't need a property manager because I live here- With the potential rent income vs monthly mortgage price, I am probably breaking even if lucky- Pro tenantJacksonville:- Total cost of home is lower, even though I will have a higher down payment because I am buying it as an investment property- With the potential rent income vs monthly mortgage price, I might make a couple hundred a month... which can eventually be used as a down for another property?

We implemented a similar program and called it an 'Owners Benefits Package,' but it didn’t go over well, so we eventually phased it out.

The biggest issue is that eventually those decks will need replacement (I’m keeping them alive as long as I can).

If you are over these amounts, you can do a backdoor contribution, which is contributing to a Traditional IRA and then immediately converting to a Roth IRA.

It goes deeper than that.NYC Liberal policies, including strong tenant protections, increases the risk of failure so much that the risk far outweighs the rewards.Financial ruin is just around the corner for the small Mom and Pop Property Investor that it doesn't make sense for them.The Tenants will have free Attorneys that are bent on delaying eviction cases so long that it stretches into years while Mom and Pop suffer from lack of rental income and still have to pay all the bills and do the management.Additionally, the increase in homeless living rough in the streets due to Sanctuary laws causing a lack of shelter beds, then evicting shelter residents after 30 days creating more homelessness, policies that tie up the Police's ability to arrest perpetrators, etc. only causes Mom and Pop to sell out at large discounts to larger Landlords who are capable to use Economies of Scale to eek out a profit.These larger Landlords will eventually turn a much higher profit as the pendulum will eventually swing towards the middle when the NYC Voting population eventually realizes that it's not a conspiracy of the Rich that's causing the Wealth Gap to increase.It's the same liberal laws that encourage people to become lifelong tenants, small Entrepreneurs (including Property Owners and small Mom and Pop Businesses) to be destroyed, and Rents to rise astronomically as housing becomes scarer even when the population declines by as much as 7% in the last several years. 

Will rents go back to their peaks and eventually past? 

Lacey asked for $20K for furnishings and another $10K to convert the garage to a play room and add a pool heater.

I personally like long term rentals, but it sounds like the numbers don't make sense and if you cant afford to or can't justify covering that much negative cash flow then another strategy is renting by the room, that works well if you have or can convert to at least 4 or 5 bedrooms. 

Local market for now but eventually I'd love to target out-of-state properties as well.