Trying to plan long-term, but where to begin

[Jonathan D.]

I am looking for some advice about what is the most responsible path to take in my situation.

I just turned 25 and would like to start investing in real-estate with the goal to create long-term value. I do not need the cashflow for daily expenses; I would rather reinvest it to grow my real estate holdings.

I have zero debt but do lease a car and rent a condo for $1000/mo. Cash for downpayments will not be an issue, though limited credit history may (good credit, just limited since I have no mortgage on record).

My main questions are:

1. My first step is to stop paying rent and getting nothing in return. My current condo I am very happy with, and is desirable for several reasons. It is in a desirable neighborhood and walking distance to dining and shopping. Renting or buying these condos is also the cheapest way to get into the neighborhood - it's the only condo development, and all of the single family homes start at around 450-500k. I have the option to purchase it for 130k, which is below market value (owner is family). I have worked some comps and it appears it could rent for $1200-1300 comfortably, but my main concern is that it has a $267 HOA attached to it that would eat directly from my profit. Is a condo in this situation automatically unrentable from a profit perspective? If that is the case, I will need to move (I can't imagine buying a condo I won't be able to later rent when I move to a house).

2. The other thing I am considering is that my area always has several condos available for sale on the same street as me that then become occupied quickly (Proctor and Gamble employees make up 80% of the clients). It would be tempting to purchase them for around 150k and develop 2-3 properties just a few feet away from my own condo. Managing the would be much easier. Plus, I have the benefit of having super-stable tennants that are professional, clean, work for P&G mostly, etc. And I already know the HOA does a great job keeping things in good shape since I've lived there for two years now. I am already familiar with the rules, regulations etc. This is also in an area that is not over-saturated with condos like downtown, and where modest (not incredible) appreciation is forecast. Again though, the kicker is the HOA. Each unit I buy will have a HOA attached.

In my situation, would you consider moving entirely out of my location or is it possible to make such an otherwise perfect situation work even with high HOA's? Any other advice would be greatly appreciated as well.