I look at real estate investing as a lifelong journey. It is my retirement plan. And I learn what I need to so that I can be better as I work toward the passive income and 10-hour work weeks lol.
If I look in the past, I was interested in real estate as a dreamer. Yes, I made goals but I didn't have everything in place. I read lots of books, then bought my own home, then in selling my own home became disgusted with Realtors I encountered. I became one to help myself first. Then bought my next home as my own Realtor, which also is my first investment property (and I got a really good deal off of the MLS. At the time it was what I could afford.) Since, I have helped friends, family, and referrals buy or sell. I found this site through my own research.
In the now, I primarily refer to 1 lender but talk to all that I encounter. I only work with lenders that I have direct access too and that answer my calls evenings and weekends. I perform DIY rehabbing when I don't understand what is involved and based on my timeline allowed. Do I want to be a contractor? No, but I want to know if I am being ripped off.
In 2018, I want to convert my current property into 2 with positive cash flow. That means that I need to get better at sourcing deals/marketing/more in-person conversations. Ironic to me, before 10/2017 I thought I could use my current property as a rental for BRRRR method though because of Fannie Mae rules (feedback from multiple lenders), I am prohibited. It's a mess. That led me to investigate 1031s, and in the fine print it is a mess. That led me to look at how capital gains taxes hits and everyone I talk to says push it off if I can. But the %s are the same, so why put off a problem that's going to come anyways. Initial thought was that if I sell mid-spring I might be rewarded. Now we have the Trump messy tax revision where the 2 years out of 5 residence rule could change to 5 out of 8, which seems to guarantee that I will get hit with huge capital gains tax anyways, so now why wait to sell? But then back to, my house is not ready to sell, lol.
That's a long answer too this question lol. The short answer is look at your long-term goals and learn what you need to for peace of mind and so you can go to the next step. As you learn, you will also become less fearful of hiring a pro or in situations where it makes more sense to pay than to do it yourself.
On this site, I run into so many people that want to side-step Realtors. It cracks me up because I get property updates every day of activity in my market. I tweak my own search any time I want, not when my Realtor gets to it. I look at it all, yes in the weeds there are some really good deals, but if I was doing it on my own without a Realtor then I would miss them. I visit properties Friday night, or any night for that matter, sometimes as late as 11pm. I look at tax rolls easily. And by watching the pro rehabbers I have learned how they are rehabbing homes for profit (in my market). I have learned how to talk to title cos to get in-depth info for pennies on the dollar. Being a Realtor is also a business for me and helps me on that end with expenses. I have also learned the land of agency as well. All Realtors are not equal. So being a Realtor is a total win for me. I am not a Realtor to make money, anyone can do that. I am a Realtor to realize profit.
Regarding other pros: In 2016, I hired my first contractor for a bathroom overhaul. In 2017, I hired my first tax pro for consulting only, I pay for print marketing services, and am looking at outsourcing much of my initial lead generation activities.
I have learned a TON from being a Realtor that I wouldn't have learned otherwise because my personal network is not that huge, that's the reality of it. Rather than ask questions and get short answers, the fact that I have a license encourages people to talk more and this helps me too.
I guess, only you can determine what helps you the most.