You may want to consider selling a stock that has lost value since you acquired it to offset the gain.unfortunately - you are not able to offset the capital gain by re-acquiring it.Did you look to see if you can get a line of credit with the Index fund as collateral?

If I were to acquire this property at the auction, am I inheriting a huge title and/or judgement mess? 

I have access to hard money.

Having a real estate license is always a bonus, as it gives you commissions, and access to the listings coming on the market very fast. 

I feel your pain @Adam Goyette, I have been working diligently on building a spreadsheet template I keep on OneDrive so I can access it from anywhere and save copies of any property I run numbers on.

My primary focus is wholesaling & acquiring rental properties.

Could anyone with access to the mls tell me what a property is worth the property address is 5612 Pontiac Rd, VIRGINIA BEACH VA 23462

Plus, I keep all documents that have ever been signed by me or them uploaded using their file system so at any time, either party can access their lease terms or rules and regulations quickly without having to dig in a drawer to find them.I highly recommend for a first time landlord.  

We're on the top floor with direct roof access. 

They will need a decent headset plus reliable and fast Internet access.