This is your ability to find the correct Micro-Markets to invest in based on how the numbers with $$$ in front "play nice" in that market using (not spending) your money (see below), and deliver the Goals from the Plan (see below...again). 

@Justin N Yurchak IMHO, where you sleep at night or having the ability to drive across town to place eyeballs on it are of little consequence compared to having a really strong team you can trust. find the best PM, realtor, title company, and CPA you can, know your numbers and your plan, and execute. the problems are the same so hire good people that fix problems and free you to spend your time doing higher income producing activities.

I don’t want to by too much too fast but also don’t squander my ability to get financing.

Aside from providing the basics (ie. listing tool to get the property published to 10+ major sites, scheduling tool to schedule viewings, tenant screening with comprehensive applications -- pulled reports from TransUnion, which include nationwide criminal background checks + credit checks + eviction history, digital lease creation tool, rent collection tool, and maintenance tracking tool), some services also offer your tenants additional capabilities which makes it an easier sell on your end when getting them to transition over (ie. their ability to report on-time rent payments to the credit bureaus; this can create an added incentive for making sure they pay that rent on time).

I don’t want to by too much too fast but also don’t squander my ability to get financing.

We have a loan option that will give you the ability to finance both, and do it with less money.

You can't do it with any real degree of accuracy.

I guess I was thinking that I would need to have the money in my business's possession somehow before making offers or to have a pre-approval letter indicating my ability to purchase the property, etc..

If some major expenses are in the near future the hoa needs to have the ability to pay them or their will be a special assessment that you will have to pay out of your cash flow.

Churchill Mortgage is a nationally known company that does this (thanks to Dave Ramsey) and I have found that a number of local and regional banks in my area also have the ability to do this.Good luck in the process, Justin!