Hence I have to pay $7k out of my pocket to recover full amount.

Remember, if you only need to get back 20% of the purchase price, there are many ways to recover that money in cash within the first year.

So, if the only cash you spent (and it should be) is your down payment, and that was only 20% of the purchase price, that's not really a lot of money to recover in the first year. 

I Have no idea how to factor in above concern of housing market dip and how long that could take to recover from, as well as the potential future rental market if I decided to rent instead of sell.

Other buildings in the area have HOA costs that are around $500+.I Have no idea how to factor in above concern of housing market dip and how long that could take to recover from, as well as the potential future rental market if I decided to rent instead of sell.Felt like my post was disjointed, but figured I’d post and add detail later.

Other buildings in the area have HOA costs that are around $500+.I Have no idea how to factor in above concern of housing market dip and how long that could take to recover from, as well as the potential future rental market if I decided to rent instead of sell.Felt like my post was disjointed, but figured I’d post and add detail later.

How many guests would you need to have before you recovered the full $280K? 

If your tenant refuses to apply for assistance, get them out and then try to apply to recover as much of the lost rent as you can and move on. 

I was recovering from surgery for a bit so I'm just getting back into it!

After the sale, he gave me about 17 back (the difference between the 60k mortgage and our agreed upon 43k price). 10 months later I’ve recovered my initial investment and I’m cash flowing 350 a month and now have around 33k equity thanks to this market.