So we will get a new home to move into on the super cheap and we can sell our house at what feels like the top of the market.

I ended up going with a STR for the first one because the cash flow was that much better.It made it a better deal for us because we can still use it occasionally when we travel to the area but still make plenty of money to cash flow more than that of buying a triplex or a quadplex.In the end it really comes down to what are your goals for the first property.

People are traveling now so it will be a seasonal summer but the market will still be hot.

I'm currently holding a W-2 job to have access to cheap, easy loans. 

Cleveland is great, but since the pricing is so cheap investors sometimes put blinders on and get themselves into trouble by not doing their proper due diligence.

If it’s a flip, I could reason the cost.If the entire house is 103V, its an internally shorted main breaker (cheap), an issue on the power companies end (free), or a shorted common from the weather-head to the main (not rewiring the whole house).

Don't overlook mileage and travel expenses.Each LLC might also file a NY state tax return.

I would also advise you hold a General Liability policy, it will be relatively cheap becuase it is a low risk policy.

Kalamazoo has a surplus of cheap older multifamily homes, so I assume they are not worth it as investments for landlords due to low rent prices.

Be warned they aren't cheap.