Is there a platform that will let me consolidate my expenses and pay them once a month?

It can prevent employees from covering up their tracks in fraud scenarios.You can erase it if you do the clean-up process, but that's so drastic it would look like you are covering up something (almost shredding papers) or it is rather drastic to consolidate your transaction information like that.Refs:QB 2012 help:QuickBooks automatically tracks all the additions, deletions, and modifications made to transactions in your data file.

(I want to come back to this)Because of that, the planning commission then suggested that I consolidate the 50X50 parcel into my existing property to the north, and then build on the 50X50 lot under the Accessory Dwelling Unit standards.

Each LLC is owned by a WY Holding Company.The subsidiary LLC's are disregarded entities and the income flows back to the holding company for consolidated banking and tax filing. 

I think you could consolidate the number of properties to buy better, more expensive properties. 

@Adam Britt - As for the student debt - any chance you consolidate through programs like Prosper / LendingTree?

So adding your wife is fine from the 1031 perspective.Sounds like you're taking the opportunity to consolidate your properties closer to where you live. 

I feel as though the combination of an economy unit and no job is a glaring red flag... seems as though the experiences above are consolidated to high value / vacation units.

As Jon points out you will need a conduit, some structured entity to consolidate the funds.

If that is the case, they would probably be operating a more consolidated team, but also, nowadays many companies start small despite their initial funding.