Oh boy. I try it stay out of these conversations, but occasionally feel compelled. I've made a few other posts on this topic over the years, so please do a search and maybe they'll come up?
My personal experience with a paid mentor changed my life. You can absolutely go the route of buying a small deal, gradually increasing in size, lose money and consider it your education, and all of the other common guidance often given. I was 45 when I discovered real estate investing and did not have that kind of time. I chose a mentor, used the information I was given, worked like crazy, and 9 years later have syndicated deals of the following sizes: 32, 78, 154, 238, 60, 216, 322, 128, and 377 units. Total purchase price of all is in excess of $160,000,000. To purchase these properties required raising over $58,000,000. The vast majority of those funds came from investors I met within the group, along with referrals from happy investors that have come along the way. I will just tell you that there was an absolutely ZERO percent chance that I would have ever done the first deal without the mentoring I paid for. Zero. I'm not saying someone else wouldn't be able to accomplish as much or more than I have on their own, but for me it was simply too overwhelming to consider using other people's money and not having an experienced expert and multiple resources to guide me. Not a chance. It was not easy, and I worked my rear off to achieve these results, but to think that I almost didn't jump in due to the cost is an incredibly scary prospect. I was so incredibly skeptical that I spent 6 months trying to shoot down the process, and find the skeletons that I was sure were hiding. I wish I had used those 6 months to buy more deals. I could've paid 10X what I did for the coaching, and it would have been the best decision ever.
I've also had the opportunity to invest in many other syndications as a totally passive investor as a result of my involvement with my mentoring group. Many (maybe even most) of these were with other new syndicators in the group that I know and trust, and they've dramatically increased our net worth. I would have had NO exposure to these otherwise.
I am not saying all programs are equal, or that they are for everyone. This is simply my personal perspective and results. I will also add that if you do not have some funds to begin with, it will certainly add difficulty, and may be a reason to follow the advice to start small. If you do have some funds to deploy, are willing to work hard, can commit the time, and are willing to deal with all the obstacles that are sure to come your way, paid mentoring can be a great option.