@Rafal Soltysekyes LV is expensive but ARVs are higher.in the midwest you can have the privilege of buying a house for 25K, fixing it up for 80K, and having it be worth... 100K.the cash flow just is NOT there anymore on a vanilla LTR with conventional financing.you would need some kind of creative strategy or competitive advantage. 

This has left me with about ~$80K real net worth mostly in weighted index funds and money market funds.

just put your price 100K over what you think it's worth and leave that on your voicemail. 

The only problem is that I don’t have 2 years worth of work history.

Might be worth paying a bit of interest on a smaller loan then having a larger tax bill, and pay it off the next year if you want it free and clear.You can also refi it in 10-15 years and not sell but pull out equity that wouldn't be taxable.

I remember helping people 10 years ago buying investment properties that were upset that 2013 pricing was so much higher than 2012 pricing.

I'm currently not a high net worth individual but have 1 investment property.

Then you can decide if it's worth it to hire an agent or try to sell on your own.

So, no way it would be worth when he did to avoid it.   

. $300/month is not worth it if you hate it.