Do you think I should talk to a professional CPA who specializes in real estate to get the best time frame on when and how to so? 

This approach can balance cash flow, manageability with a smaller initial investment and ease the learning curve while allowing for gradual scaling with the help of local real estate professionals and property management companies. 

Get your home tested by a professional in your area. 

@Jordan Northrup, the others hit on this, capital is by far the hardest part. I

Network with other professionals for insights and potential deals.

this will help with the administrative tasks (e.g. yearly 1099, pay off statements, accounting especially if the borrower pays faster) as well as helping to provide a 3rd party proof of non-payment in case you need to foreclose.Be sure to use an attorney that specializes in Notes, not necessarily a real estate attorney, to draft the paperwork and protect your interests.Good luck.

This is straight from the Chicago Association of REALTORS website:A reminder that the Chicago Residential Lease, and all of CAR’s forms and contracts, are an exclusive member benefit for use only by Chicago Association of REALTORS® members or those who are party to a transaction facilitated by a Chicago Association of REALTORS® member.

Cost segregations are complicated and are best left to professionals IMO.

Start by being thorough in your research and seek input from experienced professionals.

Even if you don't have a property to manage, you can start the conversation with them, explain what you're looking to do in their area, and they will be able to advise you on neighborhood insights, inspectors, and, once you have a property for them, have them go out for photos and videos.Regarding photos and videos, another option I've used is a 3rd party platform such as TaskRabbit.