@Shivani Brijmohan, while I cannot speak to NY, I will say in general:You should know how the property will be reassessed when you buy the property.  

Researching market trends and speaking with a local real estate agent can help you understand if prices are likely to rise or fall.

You are required to file a complete and accurate return, which means reporting the income that you earned along with atleast the direct expenses that you incurred on your rental.There are two comflicting forces - Your tax accountant wants to be aggressive with deductions because it will entitle you to paying less taxes(now or in the future).Your lender wants to see as much income as that will increase your Debt to Income Ratio(DTI).The good thing is that you can speak with your lender about 'one time expenses', that were only incurred in that year and are not reoccuring. 

Granted it is unlikely to result in a home run, but it also is less likely to fail big and negatively affect prospects for years. 

While speaking and telling him to pay rent, all of the sudden he started explaining to me that he was waiting for the lease to be renewed and then he was going to pay rent. 

A lot of Realtors will say their market is best, however, if you speak to any massive investor (not just real estate) they will all mention Colum bus.

When looking at my tax return from my CPA, the losses and gains show up on Form 4797 (Part I for the losses and the gain in Part III).I noticed that the loss from Part I was shown on schedule 1 line 4. and helped zero my taxable income in Form 1040 line 15 (I had a negative total income on line 9 and 11).

I wanted to learn so that I could 'speak the same language'.

Felt like I was speaking with a virtual assistant backed by AI.He estimated my re-roof would be half the size at double the rate quotes I got from everybody else... truly amateur hour for somebody that claimed to have done hundreds of these.I also was never able to find more than 5 property records tied to his name or to related LLCs.

However, while speaking with a company who specializes in Va assumptions, i was told that with VA is possible to assume For investment purposes and there’s no residency requirement.