Additionally, I like the lower down payment with FHA/THDA, especially if you have 3 other people paying down the note.  

I will be looking for entry level under 5 units in the next year and will be looking to get into apartments within the next few years.

You would then have to get a Letter of Environmental Protection, which will lower the value of your property and raise your insurance rates.Deleading generally costs $3000-$5000 per unit.

Bedrooms aren't horribly small - both units are split level units, so it looks bigger :)

They need only spend a few hours time of a lower paid employee to discover a retailer or community owner whose website declares, “Financing Available” to open a case that may earn them thousands, if not hundreds of thousands, of dollars worth of fines.

Having a separate checking account for each house just doesn't make sense at this level, so am I just stuck manually figuring out what house each charge goes to or is there a better way?

But I get why seasoned investors always push to buy lower maintenance buildings. 

My rate on my 401(k) loan is significantly lower than any HML and a little lower than bank rates.2) Qualifying/applying--I don't need to apply or qualify for it.

It just depends on what your expectations are.Realistically could you expect to house hack and have your mortgage payments be lower than renting?  

Once you feel you have a comfort level of understanding then begin but, don't be afraid of making mistakes just make sure they are manageable.