You have a lot of relevant questions and there is not quick answer to them without making a checklist of responses. Unless you want to spend the time researching the questions you have I would definitely hire out your accounting and tax work. On some level you need someone to data enter but on the other you need someone who is knowledgeable about construction to help you make the allocations between capital repairs and expenses. If you are networking in your area I would look for a referral. It would likely be a hassle scanning all of your receipts and records to an online service, if you can find one.
How are you doing the bookkeeping right now? Excel or quickbooks?
If you are doing it in excel - a receipt for $100 that consisted of $25 paint, $25 tools, $50 roof supplies.
can be entered into excel like
$50 roof supplies
At the end of the year you can sum up all the costs by description and provide that to your accountant.
A couple things to point out
Whether you expense an item or capitalize it will depend on several factors such as if you are increasing the useful life of the item, making it ready for a different use or making it more efficient. If you do any of these - you may have to capitalize it and depreciate it over its useful life. There are instances that you can currently expense it under the new rules that came out a couple years ago. It you are simply repairing it without doing the above its more likely a repair and currently expensed.
Another thing to take into account if you are buying a new property and fixing it up before you rent it out - those costs may have to be capitalized since you are getting the asset ready for use.
Please let me know if you have any specific questions.
Use QBs -set up a class for each property. When in doubt where an expense goes put it in miscellaneous and go over it with your accountant at least once or twice a year at minimum. A good cpa will figure it out for you. It doesn't seem this is your strongpoint so get somebody strong to help you.
John and Carl are spot on. Also consider outsourcing this function and focusing on your strengths. I see a lot of small business owners pulling their hair out over bookkeeping and losing sight of their primary business and goals.
Strengthen your strengths and hire your weaknesses.
Create Lasting Wealth Through Real Estate
Join the millions of people achieving financial freedom through the power of real estate investing