Good Morning Emily,I do not want to inundate you with too much information that it is overwhelming - but the Hilton Head Rental market is very intricate so I will try my best to give you an overview sense of it - as it comes down to many factors for each property. 

@Martin Neal I am a newbie and I am very grateful for your story and especially those intricate details of your deal.

There's a pocket of really cool homes in the historic district that you can get tax breaks on if you fix them up (intricate process) and there's a good opportunity to BRRRR in the area when that's not the case in much of Durham due to home prices but renters are there - you just have to know what the renters want :)It's also a cool little area nonetheless with great people and awesome food.

Many times landlords have ran the properties for years and they are TIRED.Based on all the listings I have had in Multifamily and the stories they tell me I would pay the fee for a great property manager.The benefit to owning a 50 unit or greater is usually you can land a 5% property management fee and the company will have a system in place versus a manager doing 1 house who is "winging it".Saturation rate for the area (competition) for your properties product mix and amenities will be key as well as proximity to jobs,transit,restaurants, medical facilities,etc.I don't worry that the property is vacant.Even in high crime areas it's all relative to price.I would not recommend buying in high crime areas for a novice.I have investor groups who do nothing but this and buy really cheap.Eventually these nodes will be redeveloped and cleaned out if you buy right but you have to know the city plans and intricate workings of the area.Don't listen to a seller telling you when occupied it rented for 600 a unit.Base your numbers off of what the market will be doing after your rehab.If rents were at 600 a unit but based on data have declined 1 percent a month and rents now are at 480 then when rehabbed in another 4 months your lease up might be at 460.Look at the big apartments to see what kind of specials and concessions they are running in the local area to lease up.We could all go on forever with suggestions.You really need to work with someone who has intimate knowledge of the area you want to invest in.When doing vacant or development deals the biggest mistake I see developers and investors make is to do rosy projections that 80% of the time do not go as planned.Plan for the worst but hope for the best.

It's amazing how with the help of this site you can learn intricate details of how to analyze a deal and run numbers, often times better than those that have been investing for years, all before doing your first deal and still lacking the actual experience of having done each step youself. 

I don't mean an intricate analysis that I would get talking to people in the neighborhood or the relator but more of trying to get a general idea when searching for properties to make sure that I'm not looking into a deal in a "war zone" high crime rate area that would be difficult to sell.  

I don't recommend holding property in a corporation unless its for resale as inventory, but I just thought Id mention it since I dont really know the intricate details of your particular scenario or goals with these properties.

When it comes to rental income (income you claim on your Schedule E), calculations are a little more intricate and quite different than income earned through regular wages or self employment.

Wholesalers are an intricate part of my business and to limit my potential and profitability because of generalizations would be idiotic and in poor judgement for my business.

I'd consider selling off a condo, but in my case my portfolio is intricately tied together and I'm loathe to do that.