Hi Jennifer,
I'm in a similar situation. I picked up a home this year in my neighborhood with the intention of renting it out after remodeling. After the remodel, I realized I could sell it for $50k more at minimum (net gain not including any taxes I would pay doing this), and people were asking me if I would sell it. For me, this was very tempting, but the cash flow was good, home was in my neighborhood, and I love the home. For me, it's now a long term rental with great tenants. Should I ever need to sell it, it will sell. I only look for homes in good neighborhoods, this current rental is a fairly high end rental, I could live there should I need to downsize. It costs more in this neighborhood, but in return I've always had great tenants (after screening of course), it appreciates at a higher value, and there's always demand to rent or buy if I need to sell at some point.
Personally I've always avoided flips because if you're in the middle of one and the market drops, you could lose money. After my situation this year, I had the following thought. If I go into a flip, and the market turns, I would keep it as a rental. That's my plan for 2020. For me personally it buys me some "insurance" in case the market crashes or slows down while I'm getting started on the flip, or rates go up, etc. driving prices down. As long as I could rent it to cover my overhead (and ideally more) I could do so until the market turned and I wanted to get cash out of it.
Ultimately for me personally, the best thing is to have cash flow properties that pay monthly, long term, and appreciate over time so that they get paid off or could be paid off by someone else, and grow in value, with tax benefits and ROI that's sky high compared to the stock market. There's no right or wrong answer to your question, it's what works best for you and your family and how much risk tolerance you have, I don't have as much tolerance as I probably should looking back on things. These are just a few thoughts I had with my experience. I hope this is helpful and wish you and your family the best. One last note, I have a 12 year old son. I am teaching him this process as well. The schools aren't going to teach it, and there are so many things I wish I could have done in my early twenties that I had no idea about (BP wasn't around back then lol). Have your kids help with some of the remodel work, show them the benefits, etc. They will have a head start that most of us would have loved to have!
-Travis