State and local municipalities have an ever-growing demand by non-landlord homeowners to reduce or eradicate STR's in their neighborhoods. The reason for this is chocked up to 2 reasons:
1. Short term rentals create rowdy and sometimes unsafe conditions in otherwise quiet and safe neighborhoods.
2. Short term rental homes/units drive up the price of homes faster than primary residences and long term rentals.
Shifting from long to short in some locations is perfectly reasonable, however I highly recommend you check out your local city's ordnances discussing the requirements for short term rentals. Additionally, you are likely subject to the TPT tax, transaction privilege tax, or a similarly named license/tax. Ensure you work that into your expenses when underwriting.
Answering your questions:
Experience - Location is really your main driver here. If your location is good, then the place will rent for both long and short. If your property sucks, people won't rent it out as a STR either. Don't listen to your agent at all, go on rentometer, airDNA, and other websites to help you make an educated decision on how your property will rent. Your agent is NOT doing this for you and is only concerned about making their commission, no matter how many cookies they send you or white their teeth are.
Cash flow - you are not guaranteed cash flow. Yes, you might have some stellar months as a STR during the year, but you might have long stretches where the property is vacant. With your research that I mentioned above, make the choice where you feel the most confident with supporting evidence. It's not a one size fits all situation. Your property must be desirable - and that desire is different for different reasons when comparing STR vs LTR.
Tips - find a good property that lies inside of a good location and has a high demand for either STR or LTR. Again, research and underwriting your deal. Again, do not listen to your RE agent's opinion on the matter. They do not care.
Moving - Sure, find an affordable place that you like and start there. You will have the exact same questions wherever you go though. If you keep waiting, you will keep finding reasons to not do it.