You're able to observe that the building is brick, and the exterior appears to be in good condition.

If most people are flying to your destination, it's much harder to get 15-30 or more people together, and those larger homes stand less of a chance.While I've done a bit of research in Galveston, definitely not enough to answer your question.Another angle to consider if it's legal from a short-term rental and ordinance perspective, buy a home with a number of large bedrooms, and create exterior doors to each of them, put in a kitchenette with a microwave and mini-fridge, and rent them separately, in particular if most/all of them can have en-suite bathrooms. 

Homes exterior is approx half brick and half vinyl siding; originally built in the 1950s.

In a multi, Landlord takes care of exterior maintenance.

They said it's too high on the exterior and slants into the middle.

Regardless of the surface...if there's lead paint on the interior/exterior of the unit and it's loose/flaking, it will need to be taken care of. 

However, there are some exterior repairs that need to happen before the VA will approve.

Your structure depends on your investors so it's important for you to understand what your investors goals, objectives, and expectations are.If you'd like some more information on this topic, it just so happens that my business partner and I recently did a talk titled 'How to Raise Private Money...Magnetically'.

In Charleston a good exterior paint job is going to cost at least 25K 

The unit is 600 sq. feet and I know we need an exterior unit of 20,000 BTUs and two indoor units.