I am considering a short sale property as my first investment prop.

Increase the character count for the PROPERTY SALES DESCRIPTION field. 

But just include this activity as part of your closing when you buy your next property.The other thing you can do is have your money lenders be part of the purchase and sale.

@Mikal Lewis do you research ahead of time, only market the contract for sale (not the property), learn more at a local real estate investing meet up, take a experienced investor out to coffee/lunch to ask questions

If the same item is on sale at Walmart you will buy it there instead of Target.

You can do a google search for a 1031 tax calculator to get a ballpark idea (you will need a few data entry points (sale price, depreciation taken, balance on the loan, 1031 fees, etc.) 

Tenant and SFH resale do not go hand in hand.Your best option is to set it up now for tenants as I suggest and then do another reno to upgrade for sale.....possibly stone, hardwood and tile to maximise profits when you sell assuming they are appropriate for your market.

Will your strategy change during the next time properties go on sale?

I have made 4 offers in the last two weeks on estate sale homes, all cash, closing in 4 days, 100k earnest money, with only due diligence as a contingency.

I have made 4 offers in the last two weeks on estate sale homes, all cash, closing in 4 days, 100k earnest money, with only due diligence as a contingency.