Need help calculating capital gains taxes if we decide to do a straight sale vs. 1031.

Was hoping it would be straight forward enough to not need a lawyer.

I have a second LLC that also brings in money, all straight pass-through money.

It's their job to document the exchange, handle the transfer of funds and consult with you to keep you on the straight and narrow.    

I use cozy.co for tenants to pay me, so I think billing back to them would be pretty straight forward through a service like that.

When I get them, I feel that I have to take time out of whatever I am doing and head straight to the bank, and I certainly don't want it known that I sometimes have large amounts of cash on me.

This way, I can discount my offer by the amount saved in broker commissions.But before I put out the ad, I prepared for those calls by creating a Seller's Questions Sheet, so I would know exactly what to say to each caller.The most important things you want to know, besides the details of the property:How much they owe.How much the property is worth.How much equity they have (the difference between property value and mortgage balance).Whether they are current or delinquent on the loan.What their motivations are (why are they willing to sell to an investor).And before I put out the ad, I also prepared by creating Seller's Categories to help me determine the buying strategy I would use based on the situation of the seller, the equity and the loan status.Once you have the info from the Seller's Questions Sheet, you can put the sellers into one of the following categories.Seller Category 1 – Delinquent + No Equity = Short Sale.Seller Category 2 – Current + No Equity = Seller Finance Rental.Seller Category 3 - Current or Delinquent + Equity = Straight Purchase.Take Seller Category 1 for instance.

One of the pieces of our system includes the hiring of a part-time bookkeeper to keep the ledgers straight in our Buildium property management software. 

It's sounding like going straight up to a property unannounced is definitely not a good idea

@Dante Farres If they're viable rentals in your market I would skip straight to a 2-4 unit :)