Get your credit, and cash reserves in a good place, be a constant learner. 

You should sign up for Sherrif auction updates like this little number going for Auction on 22 November https://www.sheriffhq.co.za/Auction/auction_detail...As a member you can see who owns it, how much was the loan and refinancing (a.k.a. bank reserve), who the banker is.Approaching people and giving them a solid deal can nett you 20% discount you need to hit the all powerful cashflow positive.Why am I sharing this great tool?

do you have the cash to do everything... plus a good 10-20% reserve?  

Also, I would make sure the condo association has strong reserves so you are not hit with a special assessment.

You also need to strongly consider  not only  the content of the forms you use but  what type of forms, your processes, your marketing, finances, your funding reserves,  landlord tenant matters, property management  issues, if you'll operate as a person or an entity, etc, etc...

But, I wanted to know if my reserved/conservative stance was warranted, or was I unnecessarily leaving money on the table. 

My long term goal is to buy and hold property to generate passive income and I thought becoming an agent might be a good way to further that goal for several reasons: 1) As an agent I'll have access to data from the MLS which will help me to learn my market, and potentially areas outside the city too. 2)  I'll likely make contacts with lawyers, CPAs, mortgage brokers and other professionals through my dealings. 3) I can write my own offers. 4) I need a career change anyways.That being said I have some reservations.

Virginia allows the landlord to accept rent with reservation and continue eviction proceedings.

.- Capital Reserve for roof, heating systems, AC(?)

@Andy Krzanowsky What do your reserves look like without the extra $8k?