I did electronic signatures on the lease through a signing service.

@Mark H.The issuer of income is the plan.Did you also withhold taxes electronically using EFTPS and report on form 945?  

Also note that you cannot simply download the 1096 - it has to be the IRS printed form, so if you don’t already have it ordered, your only way to make the deadline is to file electronically (for a fee)

One deal pays $7500 and one month costs me $350 to gather, skip and contact 500 electronic leads. 

You mention you would like to own rental properties, I would suggest to start with that, you can use the 30K as down payment on a property, self manage that property so you can learn more about that process.If the area you live in is too expensive for you to buy, look at other areas close by, even if it's an 1-2 hour drive, remember you don't have to drive there a lot, outsource maintenance and collect rent electronically, it's doable and can teach you a lot while learning on the job.

The Denver MSA has many economic clusters that are attracting investment and producing jobs: aerospace, logistics, bioscience, fashion, electronics, and infrastructure engineering. 

I am using TenantCloud - rather then having everyone pay $35 application fee - should I have a "pre-application" page for them to fill out on site or send them one electronically? 

I recommend that you stay on the safe side and do send 1099s to your wholesalers.You do not need to send 1099-MISC in these cases: You paid the contractor electronically (PayPal or Credit Card).

I tried applying for a HELOC on my primary residence, but the electronic appraisal (has some fancy name... can't remember what exactly) came back too low for the loan.I'm back at the drawing board and asking my more experienced BP community of investors what they would do in this situation? 

An elderly tenant had trouble coming down 2 flights of stairs to let in her visiting nurse -- an electronic keypad entry lock fixed that.