Going into fall and homes not selling is a common misconception. Spring, yes, is the best time to sell, but if your home is priced right from the start, it can sell anytime of year. $8500 includes what exactly? That's awful low for what you are saying with the A/C, kitchen update, clean-up (assuming paint, maybe flooring?) and general landscaping. 1500 sq.ft. home should be a 2.5 or 3 ton central air unit. If you know someone, you could get a new 2.5 ton unit, line set, a-coil, new disconnect box (if needed) installed for around $2000-$2500. If you don't have a friend in the business, it's going to fun you around $4k. Are you just going to re-use the kitchen cabinets and put a new counter top on or what exactly does the kitchen update include? I'd like to know more about what you are actually going to do. I can eat up $8500 in a kitchen with ease on a flip. What sort of clean-up are you going to perform?
You need to have someone pull comps back 1 year and look at the DOM (days on market) to determine what you should set aside for holding costs. If I were you, I'd set aside at least 6 months holding costs. I see a lot of new investors and experienced people think, 2-4 weeks rehab, 1-2 months marketing till sold... I'll have it gone in 3 months. They budget 3 months holding costs exactly to actually hold it for longer and they starts burning into your profit. Especially if you're running on a tight margin of error from the start. If they're asking $95k, ARV is $135k... factoring in 6% commission for the sale of the property, 6 months holding costs and your estimated $8500, I'd be very careful. The gross profit may look like $18k-$23k but that's not much of a margin if instead of $8500, you find out there's a structural issue and now it's $18,500. Your gross profit just dropped to $8k-$13k assuming the structural issue doesn't scare buyers and your holding costs is enough to cover the additional repairs. While that's a extreme case, it can happen. I've watched several people estimate, myself included, rehab costs to have $5k more actually be spent. It's very common for you to estimate $8500 and it take $12,500-$15,000. The little things when flipping a house that most new people miss, or don't factor in, really add up big time. If you're really wanting to pursue this house as a flip, I think you really need to study the homes currently for sale, especially the one that is pending. See what that interior looks like verse yours and the pending sale price. I'd have to say that if your $8500 rehab budget is solid, and I mean solid, I'd suggest not paying a dime over $86k. And that's if, and only if your budget for rehab is spot on. I'd try to get it for a good amount less but that's just me. If you could pay cash I'd say start out in the $70k's, financing the house is going to leave you a little less room to "low ball" the bank.
When asking about how difficult it will be to refi if not sold is a tough question to answer. People are going to tell you it won't be a problem do xyz but answering a financial question without knowing more about your financials is a hard question. If your DTI (debt-to-income) is already high now, getting a rental financed may prove to be difficult. For example you say there's enough money to clear $200-$300 net profit. That's after setting aside everything and includes PITI? Mortgage payment on lets say 75% of your stated $135k ARV with a 25 year amortization table, 4.75% interest is going to run around $577 a month. I don't have much experience with VA loans but have heard the "fees" involved are high. Lets say you rent it out for $1250-$1350 a month, after PITI, vacancy, reserves etc. you're spending give or take $1000-$1050 a month. When going through a residential loan, since this isn't on your taxes and is a hypothetical, worst case scenario, they're going to take 75% of the stated lease amount rent or appraisal rent analysis, whichever is lower. Let's say the appraiser says $1300 should be the fair market rent (picked the middle for an example), 75% is going to give you a $975 "credit" of what they'll count towards your income. So you'll only have a $25-$75 negative when calculating your DTI.
I hope my response helps answer your questions and wish you the best of luck in your adventure! Hope I was able to shed some light on a few things.