However, if there was any intent to hold for productive use in trade business or as an investment then there is a possibility that they could sell that and do a 1031 exchange into the lake front home.  

People who waste their time in viewing a house to give a price before the house is bought is either desperate for money, or does not have enough experience on the trade, both do not end up great when it comes to product.

Unless you are a GC by trade, you're biting off way too much. 

@Renard Miller I have seen cases where a landlord either didn't collect them or traded services for the deposit.

What I might suggest is to have a quick 1 page or 1 paragraph "example ballpark job quote" pitch for 1-3 small example projects for them to respond to based on something within their field/trade.

I know that usually people trade up and buy a property of equal or higher value but let's just say that you buy another property for $150,000 from the cash you received from the sale.

Remote CPAs are always great, it allows you to have confidence that you can trade information with them easily.  

I have found that looking for a person that works in one trade helps.

Hey local BPers.... up until this point my investments have been SFH and Small Multis(1-4), and I've started looking at commercial properties and was wondering if anyone knows where CAP RATES are trading at in Mariemont/Fairfax?

As you get to know some of the folks offer to trade some free labor/time to be able to shadow them and learn from them.