Trying to get started but have some questions

[Collin Vosburgh]

Hey everyone, my name is Collin. I'm from Chicago but now live in SW Michigan (Otsego). I've been trying to get into real estate investing for some time now and have been studying and researching all I could. I would like to be involved with getting multi-units for buy and hold as well as gaining enough capitol to eventually be able to flip houses. I think I have a solid plan so far but would like some feedback to make sure it's a good one.

So a few years ago I bought my first house and since have about 50k-60k in equity. Now since my family and I aren't too big on the area anymore (it's kind of secluded and not the best for kids) I'm thinking of renting it out until I get my credit back up for maybe the next year and then selling and using the money I make off of it to hopefully get a couple multi-units. It's a lot of property and has 5 bedrooms and a pool. The mortgage is sort of high so I wouldn't make a whole lot off it (if I rent for 1700-1800 I would make a couple hundred a month) but at least I would be paying it down until I sell. It would be great for maybe 3-4 roommates. It also has a large pole barn on the property that I would still use for myself to run our food truck out of which is also why I would like to hang on to the property. Also I would be able to maintain the property very easily. My fiancee would buy our next house which I would make sure also has some instant equity. And from there keep acquiring more multi-units until we're able to start buying properties to flip. Any feed back or advice would be much appreciated!

Also I've been thinking of getting a real estate license, inspector license or appraiser license. Would having any of those help or even all three? What would be best?

Thanks!!