I can not seem to find any solid guidelines on how I should make the calculation accurately given my situation.

Buyers make the mistake of trusting the "expert" because of their ad in the glossy magazine and don't go and see what the property they are buying, or at least hire an independent inspector to give them accurate information.

I am going to view a HUD foreclosure property this afternoon with a client on mine here in Connecticut and for us these are the easiest homes to access.Of course the contractor bids are going to be high because they can't tell much from those pictures so they overbid to protect downside for themselves just like you are doing by bidding without seeing the property.Find a way to get in these properties and your budget will be a lot more accurate and you will be able to see if the budget can be shaved at all.The online tools we all have access to are great and can save people a lot of time when evaluating properties, but there is no substitute for walking a property.

How would I go about accurately estimating the value of repairs without looking at the property or contacting people for the sake of time and not spending money?

Looks like your closing costs are too low, typically 5% is an accurate number.Typically you should aim for properties that follow the 50% rule, which means that your expenses should be around half of your income from rents.

You want to avoid any unnecessary bad feelings with your tenant going forward.If the above is somewhat accurate, I have a question for you.

There are ways around it though; if you live in a house you buy for at least 2 years, (and this can be a multiplex, so you could rent out the other apartments) then any profit made from selling the house is not subject to capital gains tax.The hardest part to this particular process, and honestly the boat I'm in at the moment, is getting started due to lack of overhead cash.There are also the risks of the house going unsold or unrented, but that's why you don't gamble with all the money you have in the bank.

Charge the tenant as accurately as possible.

You're on the right track, 50% is a reasonable rule of thumb, however $/unit is more accurate. 

One year can not give an accurate idea of expenses.