Agree with above.The pros are that a large portion of the rent is virtually guaranteed, that you have another party to try to work out tenant issues with, and that the tenant is a little less likely to leave since their voucher limits their housing options.The cons are the hoops to jump through to get your property inspected, it can make bookkeeping a little more complicated with a property manager, and generally lower quality tenants.We don't actively look for or shy away from Section 8. 

A company may employ a bookkeeper to handle the books.

If you were planning to use Buildium primarily for general bookkeeping in addition to the accounting your PM provides, then there are much cheaper options without all the extra features you wouldn't use.

Hiring the same individual as a contractor seems much easier (in terms of added bookkeeping workload, etc.) but for my needs I'm not confident in the IRS' litmus tests...Finally, I think that a VA would be GREAT for this, but I am having trouble finding how they are treated from a tax standpoint...  

Need recommendation for simple bookkeeping and accounting (income and expenses with running totals) software or template.

There are more bookkeeping and accounting costs yet it seems to be worth it as long as you use it to make purchases, etc. 

First off I bought a subscription to quickbooks online and hired a bookkeeper.

I can see my GPR in just a couple of clicks for my month end book keeping and it’s absolutely wonderful.

It sounds like you have a great bookkeeping/accounting system set up on the profit first model :).

Although it is cumbersome to track multiple bank accounts, my bookkeeper doesn't have to guess which property the expense goes to, because if it was on the credit or debit card for that building, then the expense is charged to that building.I personally use Quickbooks, but used Quicken for a long time.I strongly recommend that you contact each tenant, knocking on the door if you have to, and get contact info.