Rich Weese - Thanks for your input - I had the same thoughts because I want to take advantage of the low rates on multiple rentals in the future.
My goal is indeed to get out of the HOA type communities to favor the residential housing to better my investments..
To answer your questions:
1. Do you want to do more than one investment?
Yes - I plan to play monopoly in the sense of acquiring a decent number of rentals that I can eventually pay off, just like the typical buy/hold investor to live comfortably. Seems like putting more of my focus on the mid to higher end rentals would be much safer than investing in what's already 20-40 years old...
2. Is your job/income fairly safe? In this economy, I would like to say my job/income is safe. I have no other debt other than my mortgage of roughly $600 a month (which is a ton cheaper than rent in the area) - I'd eventually sell my townhome in the next 10-ish years or so - or when the market favors selling, so I can dump the capital into more SFRs...
3. Are you willing to take the risk and young enough if it fails?
I'm currently 27 and will turn 28 in the next few weeks myself - I feel like if I don't take advantage of higher risk now that I'll be kicking myself in the future for not being more risk-averse and thus improving my chances at wealth!
4. Do you have a long term strategy and plans?
Long-term strategy is very modest for today's timeframe of thought; wanting to self-manage about 10 or so F&C houses and live off a modest income (I'm very conservative and don't need much income to make a happy living) - although that's not to say my frame of thought will change as I continue to invest. But that's where I stand for now, I hope that's a good decision to say the least.
5. Do you NEED the cash flow to live on? To answer based off my conservative viewpoints, I do not currently need cashflow from real estate to live on - my current income is sustaining enough. I did question though on whether it's worth investing in the lesser properties that do have some cashflow now to better my chances of seeding future investments - but not sure on that since expenses may eat up that cashflow given those properties are older (as aforementioned 70-80k properties built in 1970's type, or cinderblock housing)... any thoughts for this one?
6. Don't buy another condo-imo. You're correct on that - I want to avoid the condos although 'technically' my townhome I own the land under it - but nontheless the townhome I'm living in now - they sell like hotcakes - last house that was on the market was only on the MLS for 4 days before being contracted - it's because the specific location I'm in is close (walking distance) to literally everything you need - but it's a bit quaint in size (1200sq ft - I'd like more space in the next home I move in, and more driveway space!)