Your best bet maybe to go to RE networking events where you can meet and get to know others like yourself.

If you live to your 70's or 80's' you will bet 50 to 60 years of free insurance, so-to-speak, and maybe even keep building cash value.

- Does the place have popcorn ceilings (8th picture, there is some texture on the ceiling) - Your hardwoods look god awful, like they need to be refinished, plus wood paneling -- yuck. (13th picture) - Probably one of the most dated kitchens I've ever seen (14th picture) - What appears to be a leak of some kind in the kitchen, top right (15th picture) - Drop ceiling...yuck (16th picture) - No pictures of bathrooms, but I bet they're a disaster.So lets recap -- this place needs a ton of work.

But I bet you won't make that same mistake again.  

Are condos safer bets than homes?

I think a triplex to fourplex would be the best bet. 

That’s your best bet to find someone to shadow.

I am not betting on seeing any noticeable appreciation any time soon.

So I think the best bet at the moment is to hold onto the condo for now and eat the $300 dollar a month loss (plus expenses/repairs/etc)  until this current lease is up next summer then attempt to raise the rent and break even while hoping it further appreciates. 

Using cash is like betting on black or red.