If Airbnb is an option for your spare bedroom then that's great, personally when I first started I didn't want to have to deal with the in and outs of people and also making my place aesthetic enough that it would rank well on Airbnb so I went straight to long term rentals but if you want to dip your toe in the water it could be a good option if shorter term tenants make you more comfortable. 

What's at risk is it may not cash flow and renting is not so common in South Jersey, but I would feel more comfortable investing in a good area where schools are decent to good, and tenants are likely to care more.

Sam you can do ground up and there's no competition. areas like florida city, homestead, Vero beach, depending on your comfort level.

Every partner I've had over the years starts there and when they're comfortable with the capital they have then they can branch and purchase some long term assetts.

If the HVAC was only 3-5 years old, I probably wouldn't think it was going out and maybe not have as much cash saved for it, but if it was 20-25 years old I would think it will die soon I better be prepared.You just need to take a look at your properties, understand the risk profile of each in terms of when certain CapEx items might need replacing, and decide if that is the risk profile you are comfortable with.

You have to decide how comfortable you feel. 

The current market environment is such that your return can't possibly make up for the penalties and taxes you would pay. 

What's at risk is it may not cash flow and renting is not so common in South Jersey, but I would feel more comfortable investing in a good area where schools are decent to good, and tenants are likely to care more.

What's at risk is it may not cash flow and renting is not so common in South Jersey, but I would feel more comfortable investing in a good area where schools are decent to good, and tenants are likely to care more.

What's at risk is it may not cash flow and renting is not so common in South Jersey, but I would feel more comfortable investing in a good area where schools are decent to good, and tenants are likely to care more.