So you’ll have that much more tax-sheltered rental income, which is always a good thing.The bottom lineAs you can see, the tax rules for vacation homes are complicated.If you have a vacation home that is rented for more than 14 days during the year and your personal use does not exceed the greater of (1) 14 days or (2) 10% of the rental days, the home is classified as a rental property for tax purposes.

Haughville is not the best area, it's what we would classify as a C/D zone. 

I also checked and it seems that the State that you want to invest in is also classified as a "Tenant Friendly" region, meaning that your renters are protected by the government in being late on their payments and you will need to wait longer in order to evict them from your property. 

I'm thinking that I need someone who can help with tax strategy (e.g. 1031s), classifying expenses properly (e.g. improvements vs. repairs/maintenance), can file my taxes, and represent me if I'm audited.Would a CPA be overkill for my situation?

@Travis Hill this is how I would classify the type of house or neighborhood:A - Rich people live here. 

While the bar is high for the court to even consider piercing the veil, the court is not going to be deterred by your entity being classified as a MMLLC rather than a SMLLC.

Would this automatically classify this as commercial?

But at that point, the other properties are so geographically distanced (~5-10 miles) that I think it would be unwise to classify them as comparable properties.How do you currently get around having limited data to work with?

I've found a great looking deal in the classified ads that is off the MLS and includes a bundle of 3 houses listed at about 70% the price of comps though I haven't seen it in person yet.Seller claims to be selling "due to health" but that's all I know at this point.  

I do not intend to use it at a duplex, but my loan officer has told me that it will probably need to be classified as a duplex, thus requiring me to put 15 percent down (as opposed to 3% down if it was a SFH).