If you're only doing a couple or so transactions per year probably ok.On the other hand, you can have more control and eliminate the need to go through a custodian for investments by the use of checkbook IRA or Solo 401k.

Then use those funds for the rehab of the other property.   

When you have a good cash on cash from day one, it means that appreciation won't be that great.There are many other factors to look at as the neighborhood and the age of the property those are going to give you a better undertanding on future growth

If it is your owner occupied house and using your home for STR and the insurance has a premium for guest damage, you are insured just like any other STR insurance. 

You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.4.

Since you're looking to expand into Florida and other states, I'd recommend starting by narrowing down your focus:Market Research – Florida has great opportunities, but each state and city has different laws, taxes, and demand drivers.

@Shiloh Lundahl I will do value add specifically with ADU development, so I am tracking permits to find other ADU developments and overall inventory growth to find a competitive edge with supplying demand in areas lacking larger residential developers aka "the middle housing"@Arlem Garcia Interesting, Tariffs will play a big role in supply chains, so it will be interesting to see how governments come to resolutions@Henry Clark Absolutely, imo gone are the days of investing for cashflow or appreciation, now it's about aligning long-term strategies with lifestyle 

Don't take a break when others are taking a break.

That allows the timing of the renting much easier as you can move into the new house, then rent the other, then refi the bridge loan into a perm loan. 

Quote from @Allison Cutlip: My boyfriend and I are closing on our first property soon which is a duplex where we will be living in one side and renting out the other.