Oh yes, lots of thoughts... First thing, I have no ida about your market. Average homes where I live go for 250k, a decent multi unit will run 60-100k/unit... So I paid 370 for a 4plex last year.
The first thing you need to realize is where you are at in your schooling. You don't have to pay someone for this... you can throw money at real estate to learn the hard way and read books from the library like I did, but most of your questions can be answered by hard learning, and then on the job training. Yes, buying a fixer from a wholesaler has tons of risk, and will likely lead to trouble, since you don't have experience doing this. To someone who does this every day, it's just a job that they understand. For example, ask me to start a website, a car lot, or a coffee shop, and it would be daunting... ask to estimate repair costs on a run down duplex, and it's something I do every day. So... if you want into this field, educate yourself. Of course, the best education is experience, so at some point you have to jump in.
The next thing is if real estate can actually make money in your area. It may not. If you're looking at a SFR that cost $250k, and the rent would be in the $1,800/month range, this is a bad investment. There will be almost no cash flow if you have it leveraged, and that's if you manage it yourself. If you put more down, you'll have cash flow, but your returns would be lower than if you put it into an index fund in the market.... bad deal for right now. However, I think there are not that many markets where you can just buy a house and sit back to cash the fatty checks. Most of the time, you have to bring value to the deal by either finding a great deal, being able to rehab the property, or taking on something bigger like a 4plex. so, to make money in Real estate, you'll probably have to learn one of these approaches. Myself, I'm shooting for the multi-unit advantage.
Lastly, is the big picture. Are you trying to quit your job next year? Do you want to keep your career and have real estate as a buffer against inflation? Do you want to live the rest of your life on a yacht in the Caribbean? These all influence what you're going to do. If you just want a retirement buffer, putting all cash down and hiring a manager is a simple way, but so are stocks. If you want to replace your income over the next ten years, you're going to have to hustle, and probably learn about rehabbing and/or multis... and do well at it. If you want to be the next Trump.... get advice from him, not me.