Starting Out - Need help with strategy

[Kevin NA]

Hi all,

Im just starting out and am realizing that the first step is to set up goals and a strategy to meet your goal. I could use some help developing my ideas.

First my situation:

I am a 38-yo single man living in BK/NYC. I have a steady 9-5 professional job decent income but under 6-figures. I have $30k in cash, $55 in liquid assets (stocks) and about $75k in illiquid (retirement accounts).

I am currently renting an apartment. I own no real estate.

I have time to dedicate to investing but not more than nights and weekends will allow.

I am not handy but willing to deal with routine maintenance if needed. Would be willing to manage my property at least to learn the ropes before going with a manager.

I am generally responsible with my finances and have good discipline when it comes to savings, etc. I would consider my risk tolerance to be slightly on the conservative side. I guess its all relative but REI terms for me this would mean not getting into complicated deals until I have the experience to understand them and not to leverage myself to the point where I couldn't handle the worst case scenario.

Goals:

Build a RE portfolio to supplement my retirement income (20-year horizon). Ultimate goal would be to live off RE income and retire a few years early.

Options and Ideas:
Buy an BK/NYC apartment and live in it. I am more or less priced out of these markets, but could possibly do it. I don’t feel this is a strong investment because the upfront capital requirements and cost to carry will make a second deal very difficult. Alternately I could buy and occupy a condo in Jersey City or Hoboken which would give me a bit more breathing room financially. Biggest upside in BK/NYC is I am sure the appreciation would be better. Downside is no cash flow.

Buy a condo in a less expensive market. I am from NJ and this would probably be my target. I dont know which town yet but would have to do my research. I could do this wholly as an investment and put 20-25% down. Upside is some cash flow, equity and relatively minor maintenance requirements.

Buy a 2-3 family in Jersey City and owner occupy. This way I could get more favorable financing. Downside is being a live-in landlord and I frankly don’t want to live there, but it’s a possibility if this puts me in line with my goal. Alternatively I could buy a multi-fam as an investment and manage from afar. I would be a train ride away and also have a car, so its fairly convenient. I lived there until recently and know my way around.

Questions:

What should I be thinking about in terms of my long term goals? I don’t want to handicap my long term goals for the sake of my first deal.

What are realistic goals for me? What are the metrics I should be looking at? My goal is vague at this point, I would like to get much more specific.

As a first time home buyer, what advantages do I have? How can I capitalize on them if my goal is investment and not just a roof over my head.

Would it be wise to invest in a property, yet pay rent elsewhere?

As you can see I could use some direction! Any help would be greatly appreciated.. thanks!