All in, his cost was $136,000.In our market with a standalone ADU, the equity would be about 1:1 immediately if he wanted to price and sell the property. 

Expected to hold 3-5 years and then sell for nice ROI (greater than 35% cash on cash return).

I’m not sure if I can sell it and do a 1031 on it to avoid taxes, or would it be better to try and rent it out as much as possible and buy the other one too and try and rent them both out.

In fact, if your tenant does poorly, it may put you in a situation where selling is the best option and you will be stuck using the agent that caused the problem in the first place! 

The vacant lot owner can't do anything with that land, so they should be willing to sell it for cheaper than market rate.

No one is going to insure you with knob and tube so you need to focus on selling or doing the rewiring.

But I know sometimes I may need to sell to get a larger lump sum up front to help with lack of any other income currently. 

We are looking to sell and wondered if it would be better to sell "turn key" with furniture and renters or turnkey with furniture or neither.

However, my CPA has a carryover capital loss worksheet for next year which pulls in losses from Schedule D / Form 8949 (sell of stocks), but not the long term capital loss from selling rental income property (on form 4797).

Listings are selling for roughly 92% of their list price on average.