@Tyler Cruz Most of the conventional lenders will let you go to 5 (or more) residential mortgages before they cap you ... some will allow 10, while some do not really care.It is important that you use the various lenders strategically, to get the most out of their offerings/comfort levels.  

Since you can find houses that make you more than your cost of money you can use as much leverage as you are comfortable.

Has Fireplace in each living room, formal dining room w/ built-ins, hardwoods under carpet in living/dining rooms, and hardwoods in bedroomsHere's what I see as the big kicker: There are $62,000 in back taxes from the last 3 years unpaid, which includes a host of assessments and vacant building fees. the owner is elderly and has early Alzheimer's, so I believe he has neglected these partially due to this and partially due to his being angry at the situation (lawsuit + city issues).ARV on the house is around $425,000 and I think I could buy it for around 35% of value and would have to pay the taxes and do all repairs/updates which I estimate would be around $60,000 total.  

Most developers are going to request the time it takes to make sure that the lot is suitable for building.Make an offer that you're comfortable with.

I would feel more comfortable about this option if you posted more details about the assets, as requested above. 

It sounds like you're looking to invest in areas you're comfortable and know well, which is a great idea, just go in eyes wide open.

You have to decide what you are comfortable with and whether or not your are ready to become a landlord.One other thing that comes to mind is you said you bought a bigger house. 

It truly depends on your business plan and your personal comfort.

Investing is slightly more comfortable now, but there is still that trepidation every time you buy a property or find a problem.  

Basically, my experience is owning my own home for about 8 years, and other than that, I'm just tired of working for the man and excited (and very nervous) to get out of my comfort zone and make a go of it in real estate.